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

General Information of Drug (ID: DR2501)
Drug Name
Alitretinoin
Synonyms
Alitretinoin; 9-CIS-RETINOIC ACID; Panretin; 9-cis-Tretinoin; Panrexin; 9-cis Retinoic Acid; 5300/3/8; Panretyn; Panretin Gel; (9cis)-retinoic acid; Toctino; 9(Z)-Retinoic acid; Panretin (TN); Alitretinoin (USAN); Alitretinoin [USAN]; Retinoic acid, 9-cis-; ALRT-1057; trans-Vitamin a acid; ALRT 1057; BAL-4079; LGD-1057; CHEMBL705; UNII-1UA8E65KDZ; AGN 192013; AGN-192013; LGD 100057; NSC-659772; 1UA8E65KDZ; Atragen; Retinova; LG-100057; ALRT1057; CCRIS 7098; CHEBI:50648; HSDB 7186; LGD1057; SHGAZHPCJJPHSC-ZVCIMWCZSA-N; Retinoic acid, cis-9,trans-13-; Tretinoin (TN); (7E,9Z,11E,13E)-retinoic acid; (2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid; NSC 659772; 9-cis-RA; Retin A (TN); LG100057; trans-Retinoate; beta-Retinoate; 9 Cis Retinoic Acid; alitretinoina; alitretinoine
Indication Kaposi sarcoma [ICD11: 2B57] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 300.4 Topological Polar Surface Area 37.3
Heavy Atom Count 22 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
449171
PubChem SID
509159 ; 584816 ; 838980 ; 3718107 ; 7978614 ; 8026464 ; 10300319 ; 11528315 ; 12014910 ; 14898408 ; 17396485 ; 17396973 ; 17486479 ; 22391507 ; 24702085 ; 24899373 ; 25622044 ; 25641192 ; 26681478 ; 26718599 ; 26755227 ; 26755228 ; 26755229 ; 26755230 ; 36890827 ; 46507356 ; 47811003 ; 47885624 ; 47885625 ; 50087219 ; 50110876 ; 50110877 ; 50110878 ; 53790163 ; 53801213 ; 56310968 ; 56313931 ; 56313962 ; 57288659 ; 57404908 ; 57571034 ; 75174291 ; 85240518 ; 85279329 ; 85788016 ; 87219231 ; 90451653 ; 92309911 ; 99300825 ; 99302343
ChEBI ID
ChEBI:50648
CAS Number
5300-03-8
TTD Drug ID
D0G3PI
Formula
C20H28O2
Canonical SMILES
CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)O)C)C
InChI
1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8-,16-14+
InChIKey
SHGAZHPCJJPHSC-ZVCIMWCZSA-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
13-cis-4-Oxoretinoic acid DM001019
6437087
Unclear - Unclear 1 [3]
13-cis-retinoic acid DM007065
5282379
Unclear - Unclear 1 [3]
4-hydroxy-9-cis-retinoic acid DM000858
20849244
Unclear - Unclear 1 [2]
4-oxo-all-trans-retinoic acid DM019948
6437063
Unclear - Unclear 1 [3]
9-cis-4-Oxoretinoic acid DM000857
9972939
Unclear - Unclear 1 [2]
Retinoic acid DM001016
444795
Unclear - Unclear 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002986 Alitretinoin 13-cis-retinoic acid Unclear - Unclear Unclear [3]
MR002987 Alitretinoin all-trans-retinoic acid Unclear - Unclear Unclear [3]
MR002988 Alitretinoin 4-oxo-9-cis-retinoic acid Unclear - Unclear CYP2C9 ... [2]
MR002989 Alitretinoin 4-oxo-13-cis-retinoic acid Unclear - Unclear Unclear [3]
MR002990 Alitretinoin 4-oxo-all-trans-retinoic acid Unclear - Unclear Unclear [3]
MR002991 Alitretinoin 4-hydroxy-9-cis-retinoic acid Unclear - Unclear CYP2C9 ... [2]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 Alitretinoin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 DailyMed : Alitretinoin
3 The single-dose pharmacokinetics of alitretinoin and its metabolites are not significantly altered in patients with cirrhosis Br J Dermatol. 2014 Feb;170(2):408-14. doi: 10.1111/bjd.12546.

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