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Cytochrome P450 2C9

ID 4757
Name Cytochrome P450 2C9
Synonyms
  • EC 1.14.13.80
  • (R)-limonene 6-monooxygenase
  • EC 1.14.13.48
  • (S)-limonene 6-monooxygenase
  • EC 1.14.13.49
  • (S)- limonene 7-monooxygenase
  • CYPIIC9
  • P450 PB-1
  • P450 MP-4/MP-8
  • S- mephenytoin 4-hydroxylase
  • P-450MP
Gene Name CYP2C9
Protein Sequence 
>Cytochrome P450 2C9
MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDISKSLTNLSKV
YGPVFTLYFGLKPIVVLHGYEAVKEALIDLGEEFSGRGIFPLAERANRGFGIVFSNGKKW
KEIRRFSLMTLRNFGMGKRSIEDRVQEEARCLVEELRKTKASPCDPTFILGCAPCNVICS
IIFHKRFDYKDQQFLNLMEKLNENIKILSSPWIQICNNFSPIIDYFPGTHNKLLKNVAFM
KSYILEKVKEHQESMDMNNPQDFIDCFLMKMEKEKHNQPSEFTIESLENTAVDLFGAGTE
TTSTTLRYALLLLLKHPEVTAKVQEEIERVIGRNRSPCMQDRSHMPYTDAVVHEVQRYID
LLPTSLPHAVTCDIKFRNYLIPKGTTILISLTSVLHDNKEFPNPEMFDPHHFLDEGGNFK
KSKYFMPFSAGKRICVGEALAGMELFLFLTSILQNFNLKSLVDPKNLDTTPVVNGFASVP
PFYQLCFIPV
Number of Residues 490
Molecular Weight 55629
Theoretical pI 7.99
GO Classification
Function
tetrapyrrole binding
binding
heme binding
monooxygenase activity
catalytic 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
oxidoreductase activity
ion binding
cation binding
transition metal ion binding
iron ion binding
Process
generation of precursor metabolites and energy
electron transport
physiological process
metabolism
cellular metabolism
General Function Involved in monooxygenase activity
Specific Function Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S- warfarin, diclofenac, phenytoin, tolbutamide and losartan
Pathways
Name SMPDB Link KEGG Link
Clopidogrel Pathway SMP00260
Cyclophosphamide Pathway SMP00447
Ifosfamide Pathway SMP00448
Reactions Not Available
Pfam Domain Function
Signals None
Transmembrane Regions None
Essentiality Non-Essential
GenBank Protein ID Not Available
UniProtKB ID P11712 Link_out
UniProtKB Entry Name CP2C9_HUMAN Link_out
PDB ID 1R9O Link_out
PDB File show
3D Structure View 3D Structure
Cellular Location Endoplasmic reticulum
Gene Sequence 
>1473 bp
ATGGATTCTCTTGTGGTCCTTGTGCTCTGTCTCTCATGTTTGCTTCTCCTTTCACTCTGG
AGACAGAGCTCTGGGAGAGGAAAACTCCCTCCTGGCCCCACTCCTCTCCCAGTGATTGGA
AATATCCTACAGATAGGTATTAAGGACATCAGCAAATCCTTAACCAATCTCTCAAAGGTC
TATGGCCCTGTGTTCACTCTGTATTTTGGCCTGAAACCCATAGTGGTGCTGCATGGATAT
GAAGCAGTGAAGGAAGCCCTGATTGATCTTGGAGAGGAGTTTTCTGGAAGAGGCATTTTC
CCACTGGCTGAAAGAGCTAACAGAGGATTTGGAATTGTTTTCAGCAATGGAAAGAAATGG
AAGGAGATCCGGCGTTTCTCCCTCATGACGCTGCGGAATTTTGGGATGGGGAAGAGGAGC
ATTGAGGACCGTGTTCAAGAGGAAGCCCGCTGCCTTGTGGAGGAGTTGAGAAAAACCAAG
GCCTCACCCTGTGATCCCACTTTCATCCTGGGCTGTGCTCCCTGCAATGTGATCTGCTCC
ATTATTTTCCATAAACGTTTTGATTATAAAGATCAGCAATTTCTTAACTTAATGGAAAAG
TTGAATGAAAACATCAAGATTTTGAGCAGCCCCTGGATCCAGATCTGCAATAATTTTTCT
CCTATCATTGATTACTTCCCGGGAACTCACAACAAATTACTTAAAAACGTTGCTTTTATG
AAAAGTTATATTTTGGAAAAAGTAAAAGAACACCAAGAATCAATGGACATGAACAACCCT
CAGGACTTTATTGATTGCTTCCTGATGAAAATGGAGAAGGAAAAGCACAACCAACCATCT
GAATTTACTATTGAAAGCTTGGAAAACACTGCAGTTGACTTGTTTGGAGCTGGGACAGAG
ACGACAAGCACAACCCTGAGATATGCTCTCCTTCTCCTGCTGAAGCACCCAGAGGTCACA
GCTAAAGTCCAGGAAGAGATTGAACGTGTGATTGGCAGAAACCGGAGCCCCTGCATGCAA
GACAGGAGCCACATGCCCTACACAGATGCTGTGGTGCACGAGGTCCAGAGATACATTGAC
CTTCTCCCCACCAGCCTGCCCCATGCAGTGACCTGTGACATTAAATTCAGAAACTATCTC
ATTCCCAAGGGCACAACCATATTAATTTCCCTGACTTCTGTGCTACATGACAACAAAGAA
TTTCCCAACCCAGAGATGTTTGACCCTCATCACTTTCTGGATGAAGGTGGCAATTTTAAG
AAAAGTAAATACTTCATGCCTTTCTCAGCAGGAAAACGGATTTGTGTGGGAGAAGCCCTG
GCCGGCATGGAGCTGTTTTTATTCCTGACCTCCATTTTACAGAACTTTAACCTGAAATCT
CTGGTTGACCCAAAGAACCTTGACACCACTCCAGTTGTCAATGGATTTGCCTCTGTGCCG
CCCTTCTACCAGCTGTGCTTCATTCCTGTCTGA
GenBank Gene ID AY341248 Link_out
GeneCard ID Not Available
GenAtlas ID CYP2C9 Link_out
HGNC ID HGNC:2623 Link_out
HPRD ID Not Available
IUPHAR ID Not Available
Guide to Pharmacology ID Not Available
Chromosome Location Not Available
Locus 10q24
SNPs CYP2C9 Link_out
General References
  1. Meehan RR, Gosden JR, Rout D, Hastie ND, Friedberg T, Adesnik M, Buckland R, van Heyningen V, Fletcher J, Spurr NK, et al.: Human cytochrome P-450 PB-1: a multigene family involved in mephenytoin and steroid oxidations that maps to chromosome 10. Am J Hum Genet. 1988 Jan;42(1):26-37. Pubmed
  2. Kimura S, Pastewka J, Gelboin HV, Gonzalez FJ: cDNA and amino acid sequences of two members of the human P450IIC gene subfamily. Nucleic Acids Res. 1987 Dec 10;15(23):10053-4. Pubmed
  3. Yasumori T, Kawano S, Nagata K, Shimada M, Yamazoe Y, Kato R: Nucleotide sequence of a human liver cytochrome P-450 related to the rat male specific form. J Biochem. 1987 Nov;102(5):1075-82. Pubmed
  4. Umbenhauer DR, Martin MV, Lloyd RS, Guengerich FP: Cloning and sequence determination of a complementary DNA related to human liver microsomal cytochrome P-450 S-mephenytoin 4-hydroxylase. Biochemistry. 1987 Feb 24;26(4):1094-9. Pubmed
  5. Ged C, Umbenhauer DR, Bellew TM, Bork RW, Srivastava PK, Shinriki N, Lloyd RS, Guengerich FP: Characterization of cDNAs, mRNAs, and proteins related to human liver microsomal cytochrome P-450 (S)-mephenytoin 4’-hydroxylase. Biochemistry. 1988 Sep 6;27(18):6929-40. Pubmed
  6. Ohgiya S, Komori M, Ohi H, Shiramatsu K, Shinriki N, Kamataki T: Six-base deletion occurring in messages of human cytochrome P-450 in the CYP2C subfamily results in reduction of tolbutamide hydroxylase activity. Biochem Int. 1992 Sep;27(6):1073-81. Pubmed
  7. Shimada T, Misono KS, Guengerich FP: Human liver microsomal cytochrome P-450 mephenytoin 4-hydroxylase, a prototype of genetic polymorphism in oxidative drug metabolism. Purification and characterization of two similar forms involved in the reaction. J Biol Chem. 1986 Jan 15;261(2):909-21. Pubmed
  8. Komori M, Hashizume T, Ohi H, Miura T, Kitada M, Nagashima K, Kamataki T: Cytochrome P-450 in human liver microsomes: high-performance liquid chromatographic isolation of three forms and their characterization. J Biochem. 1988 Dec;104(6):912-6. Pubmed
  9. Srivastava PK, Yun CH, Beaune PH, Ged C, Guengerich FP: Separation of human liver microsomal tolbutamide hydroxylase and (S)-mephenytoin 4’-hydroxylase cytochrome P-450 enzymes. Mol Pharmacol. 1991 Jul;40(1):69-79. Pubmed
Drugs
# DrugBank ID Drug Name Drug Type Drug Groups
1 DB02507 4-Hydroxy-3-[(1s)-3-Oxo-1-Phenylbutyl]-2h-Chromen-2-One small molecule experimental
2 DB01418 Acenocoumarol small molecule approved
3 DB00316 Acetaminophen small molecule approved
4 DB00945 Acetylsalicylic acid small molecule approved
5 DB06594 Agomelatine small molecule approved, investigational
6 DB00969 Alosetron small molecule approved, withdrawn
7 DB00404 Alprazolam small molecule illicit, approved, investigational
8 DB01424 Aminophenazone small molecule approved, withdrawn
9 DB01118 Amiodarone small molecule approved, investigational
10 DB00321 Amitriptyline small molecule approved
11 DB00381 Amlodipine small molecule approved
12 DB00613 Amodiaquine small molecule approved
13 DB00701 Amprenavir small molecule approved
14 DB01217 Anastrozole small molecule approved, investigational
15 DB01435 Antipyrine small molecule approved
16 DB00673 Aprepitant small molecule approved, investigational
17 DB04557 Arachidonic Acid small molecule experimental
18 DB01274 Arformoterol small molecule approved, investigational
19 DB06697 Artemether small molecule approved
20 DB01072 Atazanavir small molecule approved, investigational
21 DB01076 Atorvastatin small molecule approved
22 DB01117 Atovaquone small molecule approved
23 DB00972 Azelastine small molecule approved
24 DB00307 Bexarotene small molecule approved, investigational
25 DB01128 Bicalutamide small molecule approved
26 DB00188 Bortezomib small molecule approved, investigational
27 DB00559 Bosentan small molecule approved, investigational
28 DB00835 Brompheniramine small molecule approved
29 DB00921 Buprenorphine small molecule illicit, approved, investigational
30 DB01156 Bupropion small molecule approved
31 DB08875 Cabozantinib small molecule approved
32 DB00201 Caffeine small molecule approved
33 DB00796 Candesartan small molecule approved
34 DB01101 Capecitabine small molecule approved, investigational
35 DB00564 Carbamazepine small molecule approved, investigational
36 DB00748 Carbinoxamine small molecule approved
37 DB01136 Carvedilol small molecule approved, investigational
38 DB00482 Celecoxib small molecule approved, investigational
39 DB00439 Cerivastatin small molecule withdrawn
40 DB00446 Chloramphenicol small molecule approved
41 DB00672 Chlorpropamide small molecule approved
42 DB00169 Cholecalciferol small molecule approved, nutraceutical
43 DB00501 Cimetidine small molecule approved
44 DB00568 Cinnarizine small molecule approved
45 DB00604 Cisapride small molecule approved, withdrawn, investigational
46 DB00515 Cisplatin small molecule approved
47 DB04920 Clevidipine small molecule approved
48 DB00758 Clopidogrel small molecule approved, nutraceutical
49 DB00257 Clotrimazole small molecule approved
50 DB00363 Clozapine small molecule approved
51 DB00907 Cocaine small molecule illicit, approved
52 DB01394 Colchicine small molecule approved
53 DB01176 Cyclizine small molecule approved
54 DB00531 Cyclophosphamide small molecule approved, investigational
55 DB00091 Cyclosporine biotech approved, investigational
56 DB00250 Dapsone small molecule approved, investigational
57 DB00705 Delavirdine small molecule approved
58 DB00967 Desloratadine small molecule approved, investigational
59 DB01234 Dexamethasone small molecule approved, investigational
60 DB01191 Dexfenfluramine small molecule illicit, approved, withdrawn
61 DB00514 Dextromethorphan small molecule approved
62 DB00829 Diazepam small molecule illicit, approved
63 DB01144 Dichlorphenamide small molecule approved
64 DB00586 Diclofenac small molecule approved
65 DB00266 Dicumarol small molecule approved
66 DB00255 Diethylstilbestrol small molecule approved
67 DB00343 Diltiazem small molecule approved
68 DB01075 Diphenhydramine small molecule approved
69 DB00822 Disulfiram small molecule approved
70 DB00757 Dolasetron small molecule approved
71 DB00843 Donepezil small molecule approved
72 DB00988 Dopamine small molecule approved
73 DB00869 Dorzolamide small molecule approved
74 DB01142 Doxepin small molecule approved
75 DB00470 Dronabinol small molecule illicit, approved
76 DB00625 Efavirenz small molecule approved, investigational
77 DB00216 Eletriptan small molecule approved, investigational
78 DB00668 Epinephrine small molecule approved
79 DB01240 Epoprostenol small molecule approved
80 DB00876 Eprosartan small molecule approved
81 DB00783 Estradiol small molecule approved, investigational
82 DB00655 Estrone small molecule approved
83 DB04574 Estropipate small molecule approved
84 DB00402 Eszopiclone small molecule approved
85 DB00898 Ethanol small molecule approved
86 DB00749 Etodolac small molecule approved, investigational
87 DB01628 Etoricoxib small molecule approved, investigational
88 DB01023 Felodipine small molecule approved, investigational
89 DB01039 Fenofibrate small molecule approved
90 DB01195 Flecainide small molecule approved
91 DB00196 Fluconazole small molecule approved
92 DB04841 Flunarizine small molecule approved
93 DB01544 Flunitrazepam small molecule illicit, approved
94 DB00544 Fluorouracil small molecule approved
95 DB00472 Fluoxetine small molecule approved
96 DB00712 Flurbiprofen small molecule approved
97 DB01095 Fluvastatin small molecule approved
98 DB00176 Fluvoxamine small molecule approved, investigational
99 DB00983 Formoterol small molecule approved, investigational
100 DB01320 Fosphenytoin small molecule approved
101 DB01241 Gemfibrozil small molecule approved
102 DB01381 Ginkgo biloba small molecule approved, nutraceutical
103 DB01120 Gliclazide small molecule approved
104 DB00222 Glimepiride small molecule approved
105 DB01067 Glipizide small molecule approved
106 DB01016 Glyburide small molecule approved
107 DB01018 Guanfacine small molecule approved, investigational
108 DB00502 Haloperidol small molecule approved
109 DB01159 Halothane small molecule approved
110 DB03014 Heme small molecule experimental
111 DB03317 Heme C small molecule experimental
112 DB01355 Hexobarbital small molecule approved
113 DB00667 Histamine Phosphate small molecule approved
114 DB00062 Human Serum Albumin biotech approved
115 DB00327 Hydromorphone small molecule illicit, approved
116 DB01050 Ibuprofen small molecule approved
117 DB01177 Idarubicin small molecule approved
118 DB01181 Ifosfamide small molecule approved
119 DB00619 Imatinib small molecule approved
120 DB00224 Indinavir small molecule approved
121 DB00328 Indomethacin small molecule approved, investigational
122 DB01029 Irbesartan small molecule approved, investigational
123 DB00951 Isoniazid small molecule approved
124 DB01221 Ketamine small molecule approved
125 DB01026 Ketoconazole small molecule approved, investigational
126 DB01009 Ketoprofen small molecule approved
127 DB00448 Lansoprazole small molecule approved, investigational
128 DB01097 Leflunomide small molecule approved, investigational
129 DB00281 Lidocaine small molecule approved
130 DB01601 Lopinavir small molecule approved
131 DB00455 Loratadine small molecule approved
132 DB06725 Lornoxicam small molecule approved
133 DB00678 Losartan small molecule approved
134 DB00227 Lovastatin small molecule approved, investigational
135 DB01283 Lumiracoxib small molecule approved, investigational
136 DB00603 Medroxyprogesterone small molecule approved, investigational
137 DB00784 Mefenamic acid small molecule approved
138 DB01065 Melatonin small molecule approved, nutraceutical
139 DB00814 Meloxicam small molecule approved
140 DB00532 Mephenytoin small molecule approved
141 DB01357 Mestranol small molecule approved
142 DB00333 Methadone small molecule approved
143 DB00703 Methazolamide small molecule approved
144 DB00763 Methimazole small molecule approved
145 DB01028 Methoxyflurane small molecule approved
146 DB00916 Metronidazole small molecule approved
147 DB01110 Miconazole small molecule approved, investigational
148 DB00370 Mirtazapine small molecule approved
149 DB01171 Moclobemide small molecule approved
150 DB00745 Modafinil small molecule approved, investigational
151 DB00471 Montelukast small molecule approved
152 DB00788 Naproxen small molecule approved
153 DB00731 Nateglinide small molecule approved, investigational
154 DB00220 Nelfinavir small molecule approved
155 DB00238 Nevirapine small molecule approved
156 DB00622 Nicardipine small molecule approved
157 DB06803 Niclosamide small molecule approved
158 DB00184 Nicotine small molecule approved
159 DB01115 Nifedipine small molecule approved
160 DB04868 Nilotinib small molecule approved, investigational
161 DB00665 Nilutamide small molecule approved
162 DB06712 Nilvadipine small molecule approved
163 DB00540 Nortriptyline small molecule approved
164 DB00334 Olanzapine small molecule approved, investigational
165 DB00338 Omeprazole small molecule approved, investigational
166 DB00904 Ondansetron small molecule approved
167 DB00991 Oxaprozin small molecule approved
168 DB01229 Paclitaxel small molecule approved
169 DB00213 Pantoprazole small molecule approved
170 DB00617 Paramethadione small molecule approved
171 DB00715 Paroxetine small molecule approved, investigational
172 DB00850 Perphenazine small molecule approved
173 DB03783 Phenacetin small molecule withdrawn
174 DB01174 Phenobarbital small molecule approved
175 DB00946 Phenprocoumon small molecule approved
176 DB00191 Phentermine small molecule illicit, approved
177 DB00812 Phenylbutazone small molecule approved
178 DB00252 Phenytoin small molecule approved
179 DB01132 Pioglitazone small molecule approved, investigational
180 DB00554 Piroxicam small molecule approved, investigational
181 DB08860 Pitavastatin small molecule approved
182 DB01411 Pranlukast small molecule approved
183 DB06209 Prasugrel small molecule approved
184 DB00175 Pravastatin small molecule approved
185 DB00794 Primidone small molecule approved
186 DB01032 Probenecid small molecule approved
187 DB00396 Progesterone small molecule approved
188 DB01131 Proguanil small molecule approved
189 DB00420 Promazine small molecule approved
190 DB01069 Promethazine small molecule approved
191 DB01182 Propafenone small molecule approved
192 DB00818 Propofol small molecule approved, investigational
193 DB00647 Propoxyphene small molecule illicit, approved
194 DB00205 Pyrimethamine small molecule approved
195 DB01589 Quazepam small molecule illicit, approved
196 DB00908 Quinidine small molecule approved
197 DB00468 Quinine small molecule approved
198 DB01129 Rabeprazole small molecule approved, investigational
199 DB01045 Rifampin small molecule approved
200 DB01201 Rifapentine small molecule approved
201 DB00503 Ritonavir small molecule approved, investigational
202 DB00533 Rofecoxib small molecule withdrawn, investigational
203 DB00412 Rosiglitazone small molecule approved, investigational
204 DB01098 Rosuvastatin small molecule approved
205 DB01698 Rutin small molecule experimental
206 DB00936 Salicyclic acid small molecule approved
207 DB01232 Saquinavir small molecule approved, investigational
208 DB00418 Secobarbital small molecule approved
209 DB01037 Selegiline small molecule approved, investigational
210 DB01104 Sertraline small molecule approved
211 DB00203 Sildenafil small molecule approved, investigational
212 DB00641 Simvastatin small molecule approved
213 DB06268 Sitaxentan small molecule approved, investigational
214 DB00398 Sorafenib small molecule approved, investigational
215 DB00359 Sulfadiazine small molecule approved
216 DB06150 Sulfadimethoxine small molecule approved
217 DB00576 Sulfamethizole small molecule approved
218 DB01015 Sulfamethoxazole small molecule approved
219 DB08798 Sulfamoxole small molecule approved
220 DB00259 Sulfanilamide small molecule approved
221 DB06729 Sulfaphenazole small molecule approved
222 DB00891 Sulfapyridine small molecule approved
223 DB01138 Sulfinpyrazone small molecule approved
224 DB00263 Sulfisoxazole small molecule approved
225 DB00870 Suprofen small molecule approved
226 DB00675 Tamoxifen small molecule approved
227 DB01079 Tegaserod small molecule withdrawn, investigational
228 DB00231 Temazepam small molecule approved
229 DB00444 Teniposide small molecule approved
230 DB00469 Tenoxicam small molecule approved
231 DB00857 Terbinafine small molecule approved, investigational
232 DB00342 Terfenadine small molecule approved, withdrawn
233 DB00624 Testosterone small molecule approved, investigational
234 DB01041 Thalidomide small molecule approved, withdrawn, investigational
235 DB00277 Theophylline small molecule approved
236 DB01154 Thiamylal small molecule approved
237 DB00679 Thioridazine small molecule approved
238 DB00208 Ticlopidine small molecule approved
239 DB04831 Ticrynafen small molecule withdrawn
240 DB01007 Tioconazole small molecule approved
241 DB01124 Tolbutamide small molecule approved
242 DB00323 Tolcapone small molecule approved, withdrawn
243 DB01036 Tolterodine small molecule approved, investigational
244 DB00214 Torasemide small molecule approved
245 DB05109 Trabectedin small molecule approved, investigational
246 DB00752 Tranylcypromine small molecule approved
247 DB00374 Treprostinil small molecule approved, investigational
248 DB00755 Tretinoin small molecule approved, nutraceutical, investigational
249 DB00897 Triazolam small molecule illicit, approved, withdrawn
250 DB00347 Trimethadione small molecule approved
251 DB00440 Trimethoprim small molecule approved
252 DB00726 Trimipramine small molecule approved
253 DB00197 Troglitazone small molecule withdrawn
254 DB01361 Troleandomycin small molecule approved
255 DB00580 Valdecoxib small molecule withdrawn, investigational
256 DB00313 Valproic Acid small molecule approved, investigational
257 DB00177 Valsartan small molecule approved, investigational
258 DB00285 Venlafaxine small molecule approved
259 DB00661 Verapamil small molecule approved
260 DB00582 Voriconazole small molecule approved, investigational
261 DB00682 Warfarin small molecule approved
262 DB04898 Ximelagatran small molecule approved, withdrawn, investigational
263 DB00549 Zafirlukast small molecule approved, investigational
264 DB00943 Zalcitabine small molecule approved
265 DB00495 Zidovudine small molecule approved
266 DB00744 Zileuton small molecule approved, investigational
267 DB00425 Zolpidem small molecule approved
268 DB01198 Zopiclone small molecule approved