Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0080)
Drug Name
Ambrisentan
Synonyms
Ambrisentan; BSF 208075; BSF-208075; LU-208075; LU208075; Letairis; Volibris; HW6NV07QEC; LU 208075; (2S)-2-(4,6-dimethylpyrimidin-2-yl)oxy-3-methoxy-3,3-diphenylpropanoic acid; (S)-2-((4,6-Dimethylpyrimidin-2-yl)oxy)-3-methoxy-3,3-diphenylpropanoic acid; (S)-2-(4,6-Dimethylpyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropanoic acid; (s)-2-[(4,6-dimethylpyrimidin-2-yl)oxy]-3-methoxy-3,3-diphenylpropionic acid; 177036-94-1; CAS-177036-94-1; CHEMBL1111; DSSTox_CID_26282; DSSTox_GSID_46282; DSSTox_RID_81508; UNII-HW6NV07QEC
Indication Pulmonary hypertension [ICD11: BB01] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 378.4 Topological Polar Surface Area 81.5
Heavy Atom Count 28 Rotatable Bond Count 7
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
6918493
PubChem SID
12015371 ; 14779987 ; 17194924 ; 43529863 ; 50551569 ; 51091419 ; 53787770 ; 57371956 ; 93309673 ; 103307060 ; 104035299 ; 114788055 ; 118855302 ; 126616865 ; 126651844 ; 131302629 ; 134338642 ; 135692418 ; 137237404 ; 139988399 ; 143497715 ; 144205520 ; 152133959 ; 152238501 ; 152258462 ; 160647297 ; 160826914 ; 162011508 ; 162172038 ; 163093066 ; 163387054 ; 164824132 ; 170465143 ; 174007223 ; 175267375 ; 175426501 ; 178100778 ; 179116973 ; 185986582 ; 187071933 ; 196107821 ; 198977886 ; 198991664 ; 204430246 ; 211534802 ; 223375980 ; 223532574 ; 223704800 ; 224518792 ; 226395806
ChEBI ID
CHEBI:135949
CAS Number
177036-94-1
TTD Drug ID
D0X5ZI
Formula
C22H22N2O4
Canonical SMILES
CC1=CC(=NC(=N1)OC(C(=O)O)C(C2=CC=CC=C2)(C3=CC=CC=C3)OC)C
InChI
1S/C22H22N2O4/c1-15-14-16(2)24-21(23-15)28-19(20(25)26)22(27-3,17-10-6-4-7-11-17)18-12-8-5-9-13-18/h4-14,19H,1-3H3,(H,25,26)/t19-/m1/s1
InChIKey
OUJTZYPIHDYQMC-LJQANCHMSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
4-hydroxymethyl?ambrisentan DM016044
25183815
Oxidation - Oxidation 1 [3] , [4]
Ambrisentan glucuronide DM018030 N. A. Conjugation - Glucuronidation 1 [3]
4-hydroxymethyl?ambrisentan glucuronide DM016761
154699666
Unclear - Unclear 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009849 Ambrisentan 4-hydroxymethyl?ambrisentan Oxidation - Oxidation CYP3A4 ... [3], [4]
MR009851 Ambrisentan Ambrisentan glucuronide Conjugation - Glucuronidation UGT1A9 ... [3]
MR009850 4-hydroxymethyl?ambrisentan 4-hydroxymethyl?ambrisentan glucuronide Unclear - Unclear Unclear [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[2]
⏷ Show the Full List of 6  DME(s)
References
1 Ambrisentan was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Clinical pharmacokinetics and drug-drug interactions of endothelin receptor antagonists in pulmonary arterial hypertension. J Clin Pharmacol. 2012 Dec;52(12):1784-805.
3 Effect of ketoconazole on the pharmacokinetic profile of ambrisentan. J Clin Pharmacol. 2009 Jun;49(6):719-24.
4 Potential for pharmacokinetic interactions between ambrisentan and cyclosporine. Clin Pharmacol Ther. 2010 Oct;88(4):513-20.

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