Drug Information

General Information
Drug ID
DR00250
Drug Name
Oseltamivir
Synonyms
(-)-oseltamivir; (3R,4R,5S)-4-Acetylamino-5-amino-3-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid; (3R,4R,5S)-4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-enecarboxylic acid; 4-Acetylamino-5-amino-3-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid; Agucort; Agucort (TN); Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate; Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate; Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-pentan-3-yloxycyclohexene-1-carboxylate; Ethyl (5S,3R,4R)-4-(acetylamino)-5-amino-3-(ethylpropoxy)cyclohex-1-enecarboxylate; GS 4104; GS-4104; GS4104; OTV; Oseltamivir (INN); Oseltamivir [INN:BAN]; Oseltamivirum; Ro-64-0796; Ro-640796; Tamiflu (*Phosphate salt 1:1*); Tamiflu (TN); Tamiflu-Free; Tamvir
Drug Type
Small molecular drug
Indication Influenza virus [ICD11:1E30-1E32] Approved [1]
Therapeutic Class
Antiviral Agents
Structure
3D MOL 2D MOL
Formula
C16H28N2O4
Canonical SMILES
CCC(CC)OC1C=C(CC(C1NC(=O)C)N)C(=O)OCC
InChI
InChI=1S/C16H28N2O4/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)19/h9,12-15H,5-8,17H2,1-4H3,(H,18,19)/t13-,14+,15+/m0/s1
InChIKey
VSZGPKBBMSAYNT-RRFJBIMHSA-N
CAS Number
CAS 204255-11-8
Pharmaceutical Properties Molecular Weight 312.4 Topological Polar Surface Area 90.6
Heavy Atom Count 22 Rotatable Bond Count 8
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
XLogP
1.1
PubChem CID
65028
PubChem SID
10292 ,103375662 ,104332669 ,117576917 ,118048381 ,124893596 ,126657793 ,126681234 ,126733879 ,134338002 ,135023115 ,135811666 ,137002940 ,137236650 ,140589553 ,14825762 ,14898934 ,151982861 ,152099920 ,152258534 ,160647368 ,160963546 ,164786722 ,164831566 ,165702338 ,174006818 ,175267600 ,176484257 ,179116828 ,184546341 ,185976796 ,196109901 ,211535901 ,223556618 ,43121870 ,46507602 ,49958481 ,50123365 ,53789667 ,57315247 ,58106749 ,626306 ,75193389 ,7980209 ,8034664 ,8189453 ,85789649 ,92309047 ,93166584 ,96024993
ChEBI ID
ChEBI:7799
TTD Drug ID
D0O5NK
DT(s) Transporting This Drug MRP4 Transporter Info Multidrug resistance-associated protein 4 Substrate [2]
OAT1 Transporter Info Organic anion transporter 1 Substrate [3]
OAT3 Transporter Info Organic anion transporter 3 Substrate [3]
P-GP Transporter Info P-glycoprotein 1 Substrate [4]
PEPT1 Transporter Info Peptide transporter 1 Substrate [5]
Drug-Transporter Activity Data
Drug-Transporter Activity Data P-GP Transporter Info Km =4.2 microM LLC-PK1 cells-MDR1 [4]
PEPT1 Transporter Info Km =8590 microM Human cervical cancer cell line (Hela)-PEPT1 [5]
PEPT1 Transporter Info Km =6540 microM Human enterocyte-like 2 cells (Caco-2)-PEPT1 [5]
References
1 Oseltamivir was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Limited brain distribution of [3R,4R,5S]-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate phosphate (Ro 64-0802), a pharmacologically active form of oseltamivir, by active efflux across the blood-brain barrier mediated by organic anion transporter 3 (Oat3/Slc22a8) and multidrug resistance-associated protein 4 (Mrp4/Abcc4). Drug Metab Dispos. 2009 Feb;37(2):315-21.
3 FDA Drug Development and Drug Interactions
4 Nonclinical pharmacokinetics of oseltamivir and oseltamivir carboxylate in the central nervous system. Antimicrob Agents Chemother. 2009 Nov;53(11):4753-61.
5 Oseltamivir (tamiflu) is a substrate of peptide transporter 1. Drug Metab Dispos. 2009 Aug;37(8):1676-81.

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