Drug Information
| General Information | ||||||
|---|---|---|---|---|---|---|
| Drug ID |
DR00254
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| Drug Name |
Sitagliptin
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| Synonyms |
(2R)-4-OXO-4-[3-(TRIFLUOROMETHYL)-5,6-DIHYDRO[1,2,4]TRIAZOLO[4,3-A]PYRAZIN-7(8H)-YL]-1-(2,4,5-TRIFLUOROPHENYL)BUTAN-2-AMINE; (3R)-3-Amino-1-[3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one; (3R)-3-amino-1-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butan-1-one; (3R)-3-amino-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one; Janumet; Januvia; Januvia (TN); Januvia (merck & Co.); MK-0431; Sitagliptan; Sitagliptin (Prop.INN); Sitagliptin phosphate; Xelevia
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| Drug Type |
Small molecular drug
|
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| Indication | Type 2 diabetes [ICD11:5A11] | Approved | [1] | |||
| Therapeutic Class |
Hypoglycemic Agents
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| Structure |
|
 |
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| 3D MOL | 2D MOL | |||||
| Formula |
C16H15F6N5O
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| Canonical SMILES |
C1CN2C(=NN=C2C(F)(F)F)CN1C(=O)CC(CC3=CC(=C(C=C3F)F)F)N
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| InChI |
InChI=1S/C16H15F6N5O/c17-10-6-12(19)11(18)4-8(10)3-9(23)5-14(28)26-1-2-27-13(7-26)24-25-15(27)16(20,21)22/h4,6,9H,1-3,5,7,23H2/t9-/m1/s1
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| InChIKey |
MFFMDFFZMYYVKS-SECBINFHSA-N
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| CAS Number |
CAS 486460-32-6
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| Pharmaceutical Properties | Molecular Weight | 407.31 | Topological Polar Surface Area | 77 | ||
| Heavy Atom Count | 28 | Rotatable Bond Count | 4 | |||
| Hydrogen Bond Donor Count | 1 | Hydrogen Bond Acceptor Count | 10 | |||
| XLogP |
0.7
|
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| PubChem CID | ||||||
| PubChem SID |
103502876
,112947540
,117695427
,126669712
,126731480
,134337929
,135206675
,136339733
,137005783
,143037551
,143497677
,14904024
,152028143
,152164204
,152164205
,152238548
,152344340
,160646743
,160964592
,162201432
,16466401
,164784279
,164824529
,164846813
,165235282
,165245552
,165702336
,170499559
,174006349
,174529510
,175268642
,178102906
,179231014
,186005103
,35668584
,46393524
,46505822
,46511716
,46513917
,46530623
,48034814
,50070925
,56365842
,78231257
,7885474
,85789641
,92307950
,96025201
,9656038
,99443685
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| ChEBI ID |
ChEBI:40237
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| TTD Drug ID | ||||||
| DT(s) Transporting This Drug | 1-Oct | Transporter Info | Organic cation transporter 1 | Substrate | [2] | |
| OAT3 | Transporter Info | Organic anion transporter 3 | Substrate | [3] | ||
| P-GP | Transporter Info | P-glycoprotein 1 | Substrate | [4] | ||
| Drug-Transporter Activity Data | ||||||
| Drug-Transporter Activity Data | OAT3 | Transporter Info | Km =162 microM | Chinese hamster ovary (CHO) cells-OAT3 | [3] | |
| References | ||||||
| 1 | Sitagliptin was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019) | |||||
| 2 | 265 effect of dietary cholesterol on gallbladder bile lithogenicity and gene expression in the enterohepatic axis of non-obese gallstone and control women. Journal of Hepatology, 2009, 50(09):S105-S106. | |||||
| 3 | Transport of the dipeptidyl peptidase-4 inhibitor sitagliptin by human organic anion transporter 3, organic anion transporting polypeptide 4C1, and multidrug resistance P-glycoprotein. J Pharmacol Exp Ther. 2007 May;321(2):673-83. | |||||
| 4 | Tarascon Pocket Pharmacopoeia 2018 Classic Shirt-Pocket Edition. | |||||
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