CYP2A6: Difference between revisions

CYP2A6
Available structures
PDB	Ortholog search: PDBe RCSB
List of PDB id codes
	4RUI, 1Z10, 1Z11, 2FDU, 2FDV, 2FDW, 2FDY, 3EBS, 3T3Q, 3T3R, 4EJJ
Identifiers
Aliases	CYP2A6, CPA6, CYP2A, CYP2A3, CYPIIA6, P450C2A, P450PB, cytochrome P450 family 2 subfamily A member 6
External IDs	OMIM: 122720; MGI: 88597; HomoloGene: 85917; GeneCards: CYP2A6; OMA:CYP2A6 - orthologs
Gene location (Human)
Chr.	Chromosome 19 (human)
End	40,850,447 bp
Gene location (Mouse)
Chr.	Chromosome 7 (mouse)
End	26,542,973 bp
RNA expression pattern
	Top expressed in
	right lobe of liver; ; paraflocculus of cerebellum; ; middle frontal gyrus; ; frontal pole; ; Brodmann area 10; ; nasal epithelium; ; cerebellar vermis; ; male germ cell; ; sperm; ; thalamus;
	Top expressed in
	proximal tubule; ; human kidney; ; right kidney; ; hepatobiliary system; ; liver; ; esophagus; ; respiratory epithelium; ; thymus; ; nasal epithelium; ; olfactory epithelium;
	More reference expression data
	n/a
Gene ontology
Molecular function	iron ion binding; arachidonic acid epoxygenase activity; oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen; metal ion binding; monooxygenase activity; heme binding; oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen; enzyme binding; oxidoreductase activity; coumarin 7-hydroxylase activity; steroid hydroxylase activity;
Cellular component	organelle membrane; endoplasmic reticulum membrane; membrane; intracellular membrane-bounded organelle; endoplasmic reticulum; cytoplasmic microtubule; cytoplasm;
Biological process	steroid metabolic process; epoxygenase P450 pathway; coumarin catabolic process; coumarin metabolic process; organic acid metabolic process; xenobiotic metabolic process;
	Sources:Amigo / QuickGO
Orthologs
	1548
	13087
	ENSG00000255974
	ENSMUSG00000005547
	P11509
	P20852
	NM_000762
	NM_007812
	NP_000753
	n/a
	Wikidata
View/Edit Human	View/Edit Mouse

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Latest revision as of 04:58, 2 May 2024

Cytochrome P450 2A6 (abbreviated CYP2A6) is a member of the cytochrome P450 mixed-function oxidase system, which is involved in the metabolism of xenobiotics in the body. CYP2A6 is the primary enzyme responsible for the oxidation of nicotine and cotinine. It is also involved in the metabolism of several pharmaceuticals, carcinogens, and a number of coumarin-type alkaloids. CYP2A6 is the only enzyme in the human body that appreciably catalyzes the 7-hydroxylation of coumarin, such that the formation of the product of this reaction, 7-hydroxycoumarin, is used as a probe for CYP2A6 activity.

The CYP2A6 gene is part of a large cluster of cytochrome P450 genes from the CYP2A, CYP2B and CYP2F subfamilies on chromosome 19q. The gene was formerly referred to as CYP2A3; however, it has been renamed CYP2A6.^[5]

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles.^{[§ 1]}

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|alt=Fluorouracil (5-FU) Activity edit]]

Fluorouracil (5-FU) Activity edit

^ The interactive pathway map can be edited at WikiPathways: "FluoropyrimidineActivity_WP1601".

Distribution

CYP2A6 localizes to the endoplasmic reticulum and is found predominantly in the liver.

Variability

Significant interindividual variability in CYP2A6 apoprotein and mRNA levels has been observed.

Induction

CYP2A6 is known to be inducible by phenobarbital and rifampicin, and it is suspected that other antiepileptic drugs may also have this effect.

CYP2A6 Ligands

**Selected inducers, inhibitors and substrates of CYP2A6**
Substrates	Inhibitors	Inducers
Many Carcinogens MNAN NNK NDEA MTBE Other toxins aflatoxin B₁ (mycotoxin) 1,3-butadiene (in synthetic rubber) coumarin (anticoagulant, found in cinnamon) DCBN (herbicide) 7-ethoxycoumarin (test substrate) skatole quinoline MOCA (in polyurethane production) halothane (anaesthetic) losigamone (anticonvulsant) methoxyflurane (anaesthetic) cotinine (metabolite of nicotine) nicotine (stimulant) SM-12502 (PAF antagonist) valproic acid (anticonvulsant, mood-stabilizing) dexmedetomidine (sedative)^[6]	amiodarone (antiarrhythmic agent)^[6] amlodipine (calcium channel blocker)^[6] buprenorphine (semisynthetic opioid)^[6] clofibrate (fibrate)^[6] clotrimazole (antifungal)^[6] desipramine (tricyclic antidepressant)^[6] disulfiram (acetaldehyde dehydrogenase inhibitor)^[6] entacapone (COMT inhibitor, used in Parkinson's disease)^[6] fenofibrate (fibrate)^[6] gabapentin (anticonvulsant) grapefruit juice flavonoids isoniazid (antibacterial)^[6]^[7] ketoconazole (antifungal)^[6] letrozole (aromatase inhibitor, used in breast cancer)^[6] methimazole (antithyroid agent)^[6] methoxsalen (furanocoumarin, used in psoriasis)^[6] metyrapone (used to diagnose adrenal insufficiency)^[6] miconazole (antifungal)^[6] modafinil (wakefulness-promoting agent)^[6] nicotine (stimulant)^[6] orphenadrine (antihistamine)^[6] pilocarpine (muscarinic receptor agonist)^[6] pregabalin (anticonvulsant) selegiline (monoamine oxidase inhibitor)^[6]^[8] sulconazole (antifungal)^[6] tioconazole (antifungal)^[6] tranylcypromine (monoamine oxidase inhibitor)^[6]	Barbiturates amobarbital^[6] pentobarbital^[6] phenobarbital^[6] secobarbital^[6] rifampicin (antibacterial)^[6]

References

^ ^a ^b ^c GRCh38: Ensembl release 89: ENSG00000255974 – Ensembl, May 2017
^ ^a ^b ^c GRCm38: Ensembl release 89: ENSMUSG00000005547 – Ensembl, May 2017
^ "Human PubMed Reference:". National Center for Biotechnology Information, U.S. National Library of Medicine.
^ "Mouse PubMed Reference:". National Center for Biotechnology Information, U.S. National Library of Medicine.
^ This article incorporates public domain material from "Entrez Gene: CYP2A6 cytochrome P450, family 2, subfamily A, polypeptide 6". Reference Sequence collection. National Center for Biotechnology Information.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q ^r ^s ^t ^u ^v ^w ^x ^y ^z ^aa ^ab ^ac ^ad Lacy CF, Armstrong LL, Goldman MP, Lance LL (2007). Cytochrome P450 Enzymes: Substrates, Inhibitors, and Inducers. Hudson, OH: LexiComp Inc. pp. 1899–1912.
^ Wen X, Wang JS, Neuvonen PJ, Backman JT (2002). "Isoniazid is a mechanism-based inhibitor of cytochrome P450 1A2, 2A6, 2C19 and 3A4 isoforms in human liver microsomes". Eur. J. Clin. Pharmacol. 57 (11): 799–804. doi:10.1007/s00228-001-0396-3. PMID 11868802. S2CID 19299097.
^ Siu EC, Tyndale RF (2008). "Selegiline is a mechanism-based inactivator of CYP2A6 inhibiting nicotine metabolism in humans and mice". J. Pharmacol. Exp. Ther. 324 (3): 992–9. doi:10.1124/jpet.107.133900. PMID 18065502. S2CID 9833233.

External links

Human CPA6 genome location and CPA6 gene details page in the UCSC Genome Browser.
Human CYP2A6 genome location and CYP2A6 gene details page in the UCSC Genome Browser.

[WikiPathways-6] The interactive pathway map can be edited at WikiPathways: "FluoropyrimidineActivity_WP1601".

[refGRCh38Ensembl-1] GRCh38: Ensembl release 89: ENSG00000255974 – Ensembl, May 2017

[refGRCm38Ensembl-2] GRCm38: Ensembl release 89: ENSMUSG00000005547 – Ensembl, May 2017

[3] "Human PubMed Reference:". National Center for Biotechnology Information, U.S. National Library of Medicine.

[4] "Mouse PubMed Reference:". National Center for Biotechnology Information, U.S. National Library of Medicine.

[5] This article incorporates public domain material from "Entrez Gene: CYP2A6 cytochrome P450, family 2, subfamily A, polypeptide 6". Reference Sequence collection. National Center for Biotechnology Information.

[:0-7] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q ^r ^s ^t ^u ^v ^w ^x ^y ^z ^aa ^ab ^ac ^ad Lacy CF, Armstrong LL, Goldman MP, Lance LL (2007). Cytochrome P450 Enzymes: Substrates, Inhibitors, and Inducers. Hudson, OH: LexiComp Inc. pp. 1899–1912.

[pmid11868802-8] Wen X, Wang JS, Neuvonen PJ, Backman JT (2002). "Isoniazid is a mechanism-based inhibitor of cytochrome P450 1A2, 2A6, 2C19 and 3A4 isoforms in human liver microsomes". Eur. J. Clin. Pharmacol. 57 (11): 799–804. doi:10.1007/s00228-001-0396-3. PMID 11868802. S2CID 19299097.

[pmid18065502-9] Siu EC, Tyndale RF (2008). "Selegiline is a mechanism-based inactivator of CYP2A6 inhibiting nicotine metabolism in humans and mice". J. Pharmacol. Exp. Ther. 324 (3): 992–9. doi:10.1124/jpet.107.133900. PMID 18065502. S2CID 9833233.

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@@ Line 1: / Line 1: @@
+{{Short description|Protein-coding gene in the species Homo sapiens}}
-{{PBB|geneid=1548}}
+{{cs1 config|name-list-style=vanc}}
+{{Infobox_gene}}
 '''Cytochrome P450 2A6''' (abbreviated '''CYP2A6''') is a member of the [[cytochrome P450]] mixed-function oxidase system, which is involved in the metabolism of [[xenobiotic]]s in the body. CYP2A6 is the primary enzyme responsible for the oxidation of [[nicotine]] and [[cotinine]]. It is also involved in the metabolism of several pharmaceuticals, carcinogens, and a number of coumarin-type alkaloids. CYP2A6 is the only enzyme in the human body that appreciably catalyzes the 7-hydroxylation of [[coumarin]], such that the formation of the product of this reaction, 7-hydroxycoumarin, is used as a probe for CYP2A6 activity.
-The CYP2A6 gene is part of a large cluster of cytochrome P450 genes from the CYP2A, CYP2B and CYP2F subfamilies on chromosome 19q. The gene was formerly referred to as CYP2A3; however, it has been renamed CYP2A6.<ref>{{cite web | title = Entrez Gene: CYP2A6 cytochrome P450, family 2, subfamily A, polypeptide 6| url = http://www.ncbi.nlm.nih.gov/sites/entrez?Db=gene&Cmd=ShowDetailView&TermToSearch=1548| accessdate = }}</ref>
+The CYP2A6 gene is part of a large cluster of cytochrome P450 genes from the CYP2A, CYP2B and CYP2F subfamilies on chromosome 19q. The gene was formerly referred to as CYP2A3; however, it has been renamed CYP2A6.<ref>{{NCBI RefSeq|title = Entrez Gene: CYP2A6 cytochrome P450, family 2, subfamily A, polypeptide 6| url = https://www.ncbi.nlm.nih.gov/sites/entrez?Db=gene&Cmd=ShowDetailView&TermToSearch=1548}}</ref>
 == Interactive pathway map ==
@@ Line 20: / Line 22: @@
 ==CYP2A6 Ligands==
 {| class="wikitable" width=100%
-|+'''Selected inducers, inhibitors and substrates of CYP2A6{{Citation needed|date=October 2011}}'''
+|+'''Selected inducers, inhibitors and substrates of CYP2A6'''
 |-
 ! Substrates !! Inhibitors !! Inducers
 |- style="vertical-align: top;"
 |
-*Many [[Carcinogen]]s
+* Many [[Carcinogen]]s
 ** [[MNAN]]
-** [[NNK]] ([[procarcinogen]])
+** [[NNK]]
-** [[N-Nitrosodiethylamine|NDEA]] ([[carcinogen]])
+** [[N-Nitrosodiethylamine|NDEA]]
+** [[MTBE]]
-** [[MTBE]] ([[carcinogen]])
+* Other [[toxin]]s
-*Other [[toxin]]s
 ** [[aflatoxin]] B<sub>1</sub> ([[mycotoxin]])
 ** [[1,3-butadiene]] (in synthetic rubber)
-** [[coumarin]] (found in [[cinnamon]])
+** [[coumarin]] ([[anticoagulant]], found in [[cinnamon]])
 ** [[DCBN]] ([[herbicide]])
 ** [[7-ethoxycoumarin]] (test substrate)
@@ Line 44: / Line 46: @@
 * [[cotinine]] ([[metabolite]] of [[nicotine]])
 * [[nicotine]] ([[stimulant]])
-* [[SM-12502]] ([[platelet-activating factor|PAF]] [[receptor antagonist|antagonist]]
+* [[SM-12502]] ([[platelet-activating factor|PAF]] [[receptor antagonist|antagonist]])
 * [[valproic acid]] ([[anticonvulsant]], [[mood-stabilizing]])
+* [[dexmedetomidine]] ([[sedative]])<ref name=":0">{{cite book|title=Cytochrome P450 Enzymes: Substrates, Inhibitors, and Inducers|vauthors=Lacy CF, Armstrong LL, Goldman MP, Lance LL |publisher=LexiComp Inc|year=2007|location=Hudson, OH|pages=1899–1912}}</ref>
 ||
+* [[amiodarone]] ([[antiarrhythmic agent]])<ref name=":0" />
-* ([[grapefruit]] juice [[flavonoids]])
+* [[amlodipine]] ([[calcium channel blocker]])<ref name=":0" />
-* [[ketoconazole]] ([[Antifungal medication|antifungal]])
+* [[buprenorphine]] ([[Opioid|semisynthetic opioid]])<ref name=":0" />
-* [[methoxsalen]] (in [[psoriasis]])
+* [[clofibrate]] ([[fibrate]])<ref name=":0" />
-* [[pilocarpine]] ([[muscarinic receptor]] agonist)
-* [[tranylcypromine]] ([[antidepressant]])
+* [[clotrimazole]] ([[antifungal]])<ref name=":0" />
+* [[desipramine]] ([[tricyclic antidepressant]])<ref name=":0" />
-* [[isoniazid]]<ref name="pmid11868802">{{cite journal | vauthors = Wen X, Wang JS, Neuvonen PJ, Backman JT | title = Isoniazid is a mechanism-based inhibitor of cytochrome P450 1A2, 2A6, 2C19 and 3A4 isoforms in human liver microsomes | journal = Eur. J. Clin. Pharmacol. | volume = 57 | issue = 11 | pages = 799–804 | year = 2002 | pmid = 11868802 | doi = 10.1007/s00228-001-0396-3}}</ref>
+* [[disulfiram]] ([[acetaldehyde dehydrogenase]] inhibitor)<ref name=":0" />
-* [[selegiline]]<ref name="pmid18065502">{{cite journal | vauthors = Siu EC, Tyndale RF | title = Selegiline is a mechanism-based inactivator of CYP2A6 inhibiting nicotine metabolism in humans and mice | journal = J. Pharmacol. Exp. Ther. | volume = 324 | issue = 3 | pages = 992–9 | year = 2008 | pmid = 18065502 | doi = 10.1124/jpet.107.133900 }}</ref>
+* [[entacapone]] ([[Catechol-O-methyl transferase|COMT]] inhibitor, used in [[Parkinson's disease]])<ref name=":0" />
-* [[gabapentin]]
-* [[pregabalin]] (a [[prodrug]] of gabapentin)
+* [[fenofibrate]] ([[fibrate]])<ref name=":0" />
+* [[gabapentin]] ([[anticonvulsant]])
+* [[grapefruit]] juice [[flavonoids]]
+* [[isoniazid]] ([[Antibiotics|antibacterial]])<ref name=":0" /><ref name="pmid11868802">{{cite journal|year=2002|title=Isoniazid is a mechanism-based inhibitor of cytochrome P450 1A2, 2A6, 2C19 and 3A4 isoforms in human liver microsomes|journal=Eur. J. Clin. Pharmacol.|volume=57|issue=11|pages=799–804|doi=10.1007/s00228-001-0396-3|pmid=11868802|vauthors=Wen X, Wang JS, Neuvonen PJ, Backman JT|s2cid=19299097}}</ref>
+* [[ketoconazole]] ([[Antifungal medication|antifungal]])<ref name=":0" />
+* [[letrozole]] ([[aromatase inhibitor]], used in [[breast cancer]])<ref name=":0" />
+* [[methimazole]] ([[antithyroid agent]])<ref name=":0" />
+* [[methoxsalen]] ([[furanocoumarin]], used in [[psoriasis]])<ref name=":0" />
+* [[metyrapone]] (used to diagnose [[adrenal insufficiency]])<ref name=":0" />
+* [[miconazole]] ([[antifungal]])<ref name=":0" />
+* [[modafinil]] ([[wakefulness-promoting agent]])<ref name=":0" />
+* [[nicotine]] ([[stimulant]])<ref name=":0" />
+* [[orphenadrine]] ([[antihistamine]])<ref name=":0" />
+* [[pilocarpine]] ([[muscarinic receptor]] agonist)<ref name=":0" />
+* [[pregabalin]] ([[anticonvulsant]])
+* [[selegiline]] ([[monoamine oxidase inhibitor]])<ref name=":0" /><ref name="pmid18065502">{{cite journal|year=2008|title=Selegiline is a mechanism-based inactivator of CYP2A6 inhibiting nicotine metabolism in humans and mice|journal=J. Pharmacol. Exp. Ther.|volume=324|issue=3|pages=992–9|doi=10.1124/jpet.107.133900|pmid=18065502|vauthors=Siu EC, Tyndale RF|s2cid=9833233}}</ref>
+* [[sulconazole]] ([[antifungal]])<ref name=":0" />
+* [[tioconazole]] ([[antifungal]])<ref name=":0" />
+* [[tranylcypromine]] ([[monoamine oxidase inhibitor]])<ref name=":0" />
 ||
+* [[Barbiturate]]s
-* [[phenobarbital]] ([[anticonvulsant]])
+** [[amobarbital]]<ref name=":0" />
-* [[rifampicin]] ([[bactericidal]])
+** [[pentobarbital]]<ref name=":0" />
+** [[phenobarbital]]<ref name=":0" />
+** [[secobarbital]]<ref name=":0" />
+* [[rifampicin]] ([[Antibiotics|antibacterial]])<ref name=":0" />
 |-
 |}
+== See also ==
+* [[List of cytochrome P450 modulators]]
 ==References==
@@ Line 68: / Line 96: @@
 ==Further reading==
-{{refbegin | 2}}
+{{refbegin}}
-* {{cite journal |author=Pelkonen O, Rautio A, Raunio H, Pasanen M |title=CYP2A6: a human coumarin 7-hydroxylase |journal=Toxicology |volume=144 |issue=1–3 |pages=139–47 |year=2000 |pmid=10781881 |doi=10.1016/S0300-483X(99)00200-0}}
+* {{cite journal |vauthors=Pelkonen O, Rautio A, Raunio H, Pasanen M |title=CYP2A6: a human coumarin 7-hydroxylase |journal=Toxicology |volume=144 |issue=1–3 |pages=139–47 |year=2000 |pmid=10781881 |doi=10.1016/S0300-483X(99)00200-0}}
+* {{cite journal  | vauthors=Fernandez-Salguero P, Gonzalez FJ |title=The CYP2A gene subfamily: species differences, regulation, catalytic activities and role in chemical carcinogenesis   |journal=Pharmacogenetics |volume=5 |issue=  Special Issue|pages= S123–8 |year= 1995 |pmid= 7581481 |doi=10.1097/00008571-199512001-00013  }}
-{{PBB_Further_reading
+* {{cite journal  | vauthors=Smith G, Stubbins MJ, Harries LW, Wolf CR |title=Molecular genetics of the human cytochrome P450 monooxygenase superfamily |journal=Xenobiotica |volume=28 |issue= 12 |pages= 1129–65 |year= 1999 |pmid= 9890157 |doi=10.1080/004982598238868  }}
-| citations =
-*{{cite journal  | author=Fernandez-Salguero P, Gonzalez FJ |title=The CYP2A gene subfamily: species differences, regulation, catalytic activities and role in chemical carcinogenesis   |journal=Pharmacogenetics |volume=5 |issue=  Special Issue|pages= S123–8 |year= 1995 |pmid= 7581481 |doi=10.1097/00008571-199512001-00013  }}
+* {{cite journal  | vauthors=Pelkonen O, Rautio A, Raunio H, Pasanen M |title=CYP2A6: a human coumarin 7-hydroxylase |journal=Toxicology |volume=144 |issue= 1–3 |pages= 139–47 |year= 2000 |pmid= 10781881 |doi=10.1016/S0300-483X(99)00200-0  }}
-*{{cite journal  | author=Smith G, Stubbins MJ, Harries LW, Wolf CR |title=Molecular genetics of the human cytochrome P450 monooxygenase superfamily |journal=Xenobiotica |volume=28 |issue= 12 |pages= 1129–65 |year= 1999 |pmid= 9890157 |doi=10.1080/004982598238868  }}
+* {{cite journal  | vauthors=Tyndale RF, Sellers EM |title=Genetic variation in CYP2A6-mediated nicotine metabolism alters smoking behavior |journal=Therapeutic Drug Monitoring |volume=24 |issue= 1 |pages= 163–71 |year= 2002 |pmid= 11805739 |doi=10.1097/00007691-200202000-00026  |s2cid=12837210 }}
-*{{cite journal  | author=Pelkonen O, Rautio A, Raunio H, Pasanen M |title=CYP2A6: a human coumarin 7-hydroxylase |journal=Toxicology |volume=144 |issue= 1–3 |pages= 139–47 |year= 2000 |pmid= 10781881 |doi=10.1016/S0300-483X(99)00200-0  }}
+* {{cite journal  | vauthors=Xu C, Goodz S, Sellers EM, Tyndale RF |title=CYP2A6 genetic variation and potential consequences |journal=Adv. Drug Deliv. Rev. |volume=54 |issue= 10 |pages= 1245–56 |year= 2003 |pmid= 12406643 |doi=10.1016/S0169-409X(02)00065-0  }}
-*{{cite journal  | author=Tyndale RF, Sellers EM |title=Genetic variation in CYP2A6-mediated nicotine metabolism alters smoking behavior |journal=Therapeutic drug monitoring |volume=24 |issue= 1 |pages= 163–71 |year= 2002 |pmid= 11805739 |doi=10.1097/00007691-200202000-00026  }}
+* {{cite journal  | vauthors=Kamataki T, Fujieda M, Kiyotani K |title=Genetic polymorphism of CYP2A6 as one of the potential determinants of tobacco-related cancer risk |journal=Biochem. Biophys. Res. Commun. |volume=338 |issue= 1 |pages= 306–10 |year= 2005 |pmid= 16176798 |doi= 10.1016/j.bbrc.2005.08.268 |display-authors=etal}}
-*{{cite journal  | author=Xu C, Goodz S, Sellers EM, Tyndale RF |title=CYP2A6 genetic variation and potential consequences |journal=Adv. Drug Deliv. Rev. |volume=54 |issue= 10 |pages= 1245–56 |year= 2003 |pmid= 12406643 |doi=10.1016/S0169-409X(02)00065-0  }}
+* {{cite journal  | vauthors=Maurice M, Emiliani S, Dalet-Beluche I |title=Isolation and characterization of a cytochrome P450 of the IIA subfamily from human liver microsomes |journal=Eur. J. Biochem. |volume=200 |issue= 2 |pages= 511–7 |year= 1991 |pmid= 1889415 |doi=10.1111/j.1432-1033.1991.tb16212.x  |display-authors=etal}}
-*{{cite journal  | author=Kamataki T, Fujieda M, Kiyotani K |title=Genetic polymorphism of CYP2A6 as one of the potential determinants of tobacco-related cancer risk |journal=Biochem. Biophys. Res. Commun. |volume=338 |issue= 1 |pages= 306–10 |year= 2005 |pmid= 16176798 |doi= 10.1016/j.bbrc.2005.08.268 |display-authors=etal}}
+* {{cite journal  | vauthors=Yun CH, Shimada T, Guengerich FP |title=Purification and characterization of human liver microsomal cytochrome P-450 2A6 |journal=Mol. Pharmacol. |volume=40 |issue= 5 |pages= 679–85 |year= 1991 |pmid= 1944238 }}
-*{{cite journal  | author=Maurice M, Emiliani S, Dalet-Beluche I |title=Isolation and characterization of a cytochrome P450 of the IIA subfamily from human liver microsomes |journal=Eur. J. Biochem. |volume=200 |issue= 2 |pages= 511–7 |year= 1991 |pmid= 1889415 |doi=10.1111/j.1432-1033.1991.tb16212.x  |display-authors=etal}}
+* {{cite journal  | vauthors=Yamano S, Tatsuno J, Gonzalez FJ |title=The CYP2A3 gene product catalyzes coumarin 7-hydroxylation in human liver microsomes |journal=Biochemistry |volume=29 |issue= 5 |pages= 1322–9 |year= 1990 |pmid= 2322567 |doi=10.1021/bi00457a031  }}
-*{{cite journal  | author=Yun CH, Shimada T, Guengerich FP |title=Purification and characterization of human liver microsomal cytochrome P-450 2A6 |journal=Mol. Pharmacol. |volume=40 |issue= 5 |pages= 679–85 |year= 1991 |pmid= 1944238 |doi=  }}
+* {{cite journal  | vauthors=Miles JS, Bickmore W, Brook JD |title=Close linkage of the human cytochrome P450IIA and P450IIB gene subfamilies: implications for the assignment of substrate specificity |journal=Nucleic Acids Res. |volume=17 |issue= 8 |pages= 2907–17 |year= 1989 |pmid= 2726448 |doi=10.1093/nar/17.8.2907  | pmc=317701  |display-authors=etal}}
-*{{cite journal  | author=Yamano S, Tatsuno J, Gonzalez FJ |title=The CYP2A3 gene product catalyzes coumarin 7-hydroxylation in human liver microsomes |journal=Biochemistry |volume=29 |issue= 5 |pages= 1322–9 |year= 1990 |pmid= 2322567 |doi=10.1021/bi00457a031  }}
+* {{cite journal  | vauthors=Yamano S, Nagata K, Yamazoe Y |title=cDNA and deduced amino acid sequences of human P450 IIA3 (CYP2A3) |journal=Nucleic Acids Res. |volume=17 |issue= 12 |pages= 4888 |year= 1989 |pmid= 2748347 |doi=10.1093/nar/17.12.4888  | pmc=318052  |display-authors=etal}}
-*{{cite journal  | author=Miles JS, Bickmore W, Brook JD |title=Close linkage of the human cytochrome P450IIA and P450IIB gene subfamilies: implications for the assignment of substrate specificity |journal=Nucleic Acids Res. |volume=17 |issue= 8 |pages= 2907–17 |year= 1989 |pmid= 2726448 |doi=10.1093/nar/17.8.2907  | pmc=317701  |display-authors=etal}}
+* {{cite journal  | vauthors=Phillips IR, Shephard EA, Ashworth A, Rabin BR |title=Isolation and sequence of a human cytochrome P-450 cDNA clone |journal=Proc. Natl. Acad. Sci. U.S.A. |volume=82 |issue= 4 |pages= 983–7 |year= 1985 |pmid= 3856261 |doi=10.1073/pnas.82.4.983  | pmc=397177  |bibcode=1985PNAS...82..983P |doi-access=free }}
-*{{cite journal  | author=Yamano S, Nagata K, Yamazoe Y |title=cDNA and deduced amino acid sequences of human P450 IIA3 (CYP2A3) |journal=Nucleic Acids Res. |volume=17 |issue= 12 |pages= 4888 |year= 1989 |pmid= 2748347 |doi=10.1093/nar/17.12.4888  | pmc=318052  |display-authors=etal}}
+* {{cite journal  | vauthors=Wainwright BJ, Watson EK, Shephard EA, Phillips IR |title=RFLP for a human cytochrome P-450 gene at 19q13.1-qter (HGM8 provisional designation CYPI) |journal=Nucleic Acids Res. |volume=13 |issue= 12 |pages= 4610 |year= 1985 |pmid= 4011450 |doi=10.1093/nar/13.12.4610  | pmc=321810  }}
-*{{cite journal  | author=Phillips IR, Shephard EA, Ashworth A, Rabin BR |title=Isolation and sequence of a human cytochrome P-450 cDNA clone |journal=Proc. Natl. Acad. Sci. U.S.A. |volume=82 |issue= 4 |pages= 983–7 |year= 1985 |pmid= 3856261 |doi=10.1073/pnas.82.4.983  | pmc=397177  }}
+* {{cite journal  | vauthors=Fernandez-Salguero P, Hoffman SM, Cholerton S |title=A genetic polymorphism in coumarin 7-hydroxylation: sequence of the human CYP2A genes and identification of variant CYP2A6 alleles |journal=Am. J. Hum. Genet. |volume=57 |issue= 3 |pages= 651–60 |year= 1995 |pmid= 7668294 | pmc=1801261  |display-authors=etal}}
-*{{cite journal  | author=Wainwright BJ, Watson EK, Shephard EA, Phillips IR |title=RFLP for a human cytochrome P-450 gene at 19q13.1-qter (HGM8 provisional designation CYPI) |journal=Nucleic Acids Res. |volume=13 |issue= 12 |pages= 4610 |year= 1985 |pmid= 4011450 |doi=10.1093/nar/13.12.4610  | pmc=321810  }}
+* {{cite journal  | vauthors=Ding S, Lake BG, Friedberg T, Wolf CR |title=Expression and alternative splicing of the cytochrome P-450 CYP2A7  | series=306 |journal=Biochem. J. |volume=( Pt 1) |pages= 161–6 |year= 1995 |issue=Pt 1 |pmid= 7864805 |doi=  10.1042/bj3060161| pmc=1136496  }}
-*{{cite journal  | author=Fernandez-Salguero P, Hoffman SM, Cholerton S |title=A genetic polymorphism in coumarin 7-hydroxylation: sequence of the human CYP2A genes and identification of variant CYP2A6 alleles |journal=Am. J. Hum. Genet. |volume=57 |issue= 3 |pages= 651–60 |year= 1995 |pmid= 7668294 |doi=  | pmc=1801261  |display-authors=etal}}
+* {{cite journal  | vauthors=Hoffman SM, Fernandez-Salguero P, Gonzalez FJ, Mohrenweiser HW |title=Organization and evolution of the cytochrome P450 CYP2A-2B-2F subfamily gene cluster on human chromosome 19 |journal=J. Mol. Evol. |volume=41 |issue= 6 |pages= 894–900 |year= 1996 |pmid= 8587134 |doi=  10.1007/bf00173169|s2cid=12153961 }}
-*{{cite journal  | author=Ding S, Lake BG, Friedberg T, Wolf CR |title=Expression and alternative splicing of the cytochrome P-450 CYP2A7  | series=306 |journal=Biochem. J. |volume=( Pt 1) |issue=  |pages= 161–6 |year= 1995 |pmid= 7864805 |doi=  | pmc=1136496  }}
+* {{cite journal  | vauthors=Hadidi H, Zahlsen K, Idle JR, Cholerton S |title=A single amino acid substitution (Leu160His) in cytochrome P450 CYP2A6 causes switching from 7-hydroxylation to 3-hydroxylation of coumarin |journal=Food Chem. Toxicol. |volume=35 |issue= 9 |pages= 903–7 |year= 1998 |pmid= 9409631 |doi= 10.1016/S0278-6915(97)00066-5  }}
-*{{cite journal  | author=Hoffman SM, Fernandez-Salguero P, Gonzalez FJ, Mohrenweiser HW |title=Organization and evolution of the cytochrome P450 CYP2A-2B-2F subfamily gene cluster on human chromosome 19 |journal=J. Mol. Evol. |volume=41 |issue= 6 |pages= 894–900 |year= 1996 |pmid= 8587134 |doi=  10.1007/bf00173169}}
+* {{cite journal  | vauthors=Oscarson M, Gullstén H, Rautio A |title=Genotyping of human cytochrome P450 2A6 (CYP2A6), a nicotine C-oxidase |journal=FEBS Lett. |volume=438 |issue= 3 |pages= 201–5 |year= 1998 |pmid= 9827545 |doi=10.1016/S0014-5793(98)01297-6  |bibcode=1998FEBSL.438..201O |s2cid=1250823 |display-authors=etal}}
-*{{cite journal  | author=Hadidi H, Zahlsen K, Idle JR, Cholerton S |title=A single amino acid substitution (Leu160His) in cytochrome P450 CYP2A6 causes switching from 7-hydroxylation to 3-hydroxylation of coumarin |journal=Food Chem. Toxicol. |volume=35 |issue= 9 |pages= 903–7 |year= 1998 |pmid= 9409631 |doi= 10.1016/S0278-6915(97)00066-5  }}
-*{{cite journal  | author=Oscarson M, Gullstén H, Rautio A |title=Genotyping of human cytochrome P450 2A6 (CYP2A6), a nicotine C-oxidase |journal=FEBS Lett. |volume=438 |issue= 3 |pages= 201–5 |year= 1998 |pmid= 9827545 |doi=10.1016/S0014-5793(98)01297-6  |display-authors=etal}}
-}}
 {{refend}}
+==External links==
+* {{UCSC gene info|CPA6}}
+* {{UCSC gene info|CYP2A6}}
 {{PDB Gallery|geneid=1548}}
 {{Cytochrome P450}}
 {{Enzymes}}
-{{Portal bar|Molecular and Cellular Biology|border=no}}
+{{Portal bar|Biology|border=no}}
-{{PBB Controls
-| update_page = yes
-| require_manual_inspection = no
-| update_protein_box = yes
-| update_summary = no
-| update_citations = yes
-}}
-[[Category:Cytochrome P450]]
+[[Category:Cytochrome P450|2]]

v t e Cytochromes, oxygenases: cytochrome P450 (Most belong to EC 1.14)
CYP1	A1 A2 A5 B1
CYP2	A6 A7 A13 B6 C8 C9 C18 C19 D6 E1 F1 J2 R1 S1 U1 W1
CYP3 (CYP3A)	A4 A5 A7 A37 A43
CYP4	A11 A22 B1 F2 F3 F8 F11 F12 F22 V2 X1 Z1
CYP5-20	CYP5 (A1) CYP6 (G1, M2) CYP7 (A1, B1) CYP8 (A1, B1) CYP9 CYP10 CYP11 (A1, A2, B1, B2, B3, C1) CYP12 CYP13 CYP14 CYP15 CYP16 CYP17 (A1) CYP18 CYP19 (A1) CYP20 (A1)
CYP21-49	CYP21 (A2) CYP22 (A1) CYP23 CYP24 (A1) CYP25 CYP26 (A1, B1, C1) CYP27 (A1, B1, C1) CYP28 (A1) CYP29 CYP35 (B1) CYP39 (A1) CYP46 (A1)
CYP51-69	CYP51 (A1, F1) CYP52 CYP53 A1 CYP55 A1 CYP56 A1 CYP61
CYP71-99	CYP71 (C1, C2, C3, C4, Z6, AJ4, AV1, BA1) CYP72A1 CYP73A1 CYP74 (D1) CYP75 (A1, B1) CYP76 (B6, M7) CYP79 (A1, A2, B1, B2, B3, D1, D2, D3, D4) CYP80 (A1, B1, G2) CYP81 (E1, E3, E7, E9) CYP88D6 CYP90C1 CYP93E1 CYP97C1 CYP99A3
CYP101-281	CYP101A1 CYP102A1 CYP105 A1 D7 CYP106A2 CYP107 A1 G1 CYP109 B1 E1 CYP111 CYP113A1 CYP119A1 CYP123 CYP125A1 CYP139 CYP147 CYP152 A1 B1 CYP154C3 CYP158A CYP161C CYP170 A1 B1 CYP176A1 CYP183A CYP197 CYP199A2 CYP255A
CYP301-499	CYP303A1 CYP305 M2 Halloween genes ( CYP302A1, CYP306A1, CYP307A1, CYP307A2, CYP314A1, CYP315A1) CYP318A1
CYP501-699	CYP503 CYP504B1
CYP701-999	CYP704B22 CYP710 CYP720A1

v t e Enzymes
Activity	Active site Binding site Catalytic triad Oxyanion hole Enzyme promiscuity Diffusion-limited enzyme Cofactor Enzyme catalysis
Regulation	Allosteric regulation Cooperativity Enzyme inhibitor Enzyme activator
Classification	EC number Enzyme superfamily Enzyme family List of enzymes
Kinetics	Enzyme kinetics Eadie–Hofstee diagram Hanes–Woolf plot Lineweaver–Burk plot Michaelis–Menten kinetics
Types	EC1 Oxidoreductases (list) EC2 Transferases (list) EC3 Hydrolases (list) EC4 Lyases (list) EC5 Isomerases (list) EC6 Ligases (list) EC7 Translocases (list)