Tamiflu

Osteltamivir phosphate · Oseltamivir Phosphate (200 mg) · (3R,5S)-ethyl 4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate phosphate · (3R,4R,5S)-ethyl 4-acetaMido-5-aMino-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate phosphate · SOT · Oselt · CS-1978 · Oseltamivir PH

https://huagongshe.com/ko/chemical/78000

식별자 및 물리적 특성

CAS No.	204255-11-8
분자식	C16H31N2O8P
평균 분자량	410.4 g/mol
단동위원소 질량	410.18180258 g/mol
SMILES	CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1.O=P(O)(O)O
InChIKey	PGZUMBJQJWIWGJ-ONAKXNSWSA-N
PubChem CID	78000
ChEMBL	CHEMBL1200340
ChEBI	CHEBI:7799
DTXSID	DTXSID0044230

화학 및 물리적 성질

극성 표면적	168
수소 결합 공여자 수	5
수소 결합 수용자 수	9
회전 가능 결합 수	8
무거운 원자 수	27
형식 전하	0
복잡도	468
Human Drugs	Breast FeedingLactationMilk, HumanAnti-Infective AgentsAntiviral AgentsNeuraminidase InhibitorsFDA approved drugs -> Active ingredientEMA approved medicines: Human medicine
녹는점	196-198°C
저장 조건	2-8°C
용해도	H2O: 가용성30mg/mL, 투명
물리적 상태	가루
색상	흰색에서 베이지색
용해도	Soluble in water (75 mM)
BCS Class	1 (CLogP), 3 (LogP)
주요 응용	제약소분자 약용
InChI	InChI=1/C16H28N2O4.H3O4P/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)191-5(2,3)4/h9,12-15H,5-8,17H2,1-4H3,(H,18,19)(H3,1,2,3,4)/t13-,14+,15+/s3
InChIKey	PGZUMBJQJWIWGJ-IFAKAUOZSA-N
SMILES	[C@@H]1(OC(CC)CC)C=C(C[C@H](N)[C@H]1NC(=O)C)C(=O)OCC.OP(O)(O)=O \|&1:0,10,12,r\|

화학적 성질

White Cyrstalline Solid. It is freely soluble in water.

안전 및 규제

Drug Induced Liver Injury	Drug Induced Liver Injury Rank (DILIrank 2.0)Oseltamivir phosphatevLess-DILI-concern3Adverse reactionsDOI:10.1016/j.drudis.2016.02.015
Effects During Pregnancy and Lactation	◉ Summary of Use during Lactation
수질 위해 등급(WGK)	WGK 3
관세 코드	2924299500
위험 등급	IRRITANTAquatic Chronic 3Eye Irrit. 2Skin Sens. 1
저장 분류	11 - Combustible Solids

용도

개요

Oseltamivir phosphate (Tamiflu) was launched in the US and Switzerland for the treatment of influenza infections by all common strain viruses. It is an oral anti-viral drug approved for the treatment of acute, uncomplicated influenza in patients 2 weeks of age and older whose flu symptoms have not lasted more than two days. This product is approved to treat Type A and B influenza; however, the majority of patients included in the studies were infected with type A, the most common in the U.S. Efficacy of Tamiflu in the treatment of influenza in subjects with chronic cardiac disease and/or respiratory disease has not been established.

용도

Oseltamivir phosphate (Tamiflu) is a competitive neuraminidase inhibitor. The prodrug oseltamivir phosphate (Tamiflu) is itself not virally effective; however, once in the liver, it is converted by natural chemical processes, hydrolysed hepatically to its

일반 설명

receptor site showed clearly that additional binding sitesexist for the C-5 acetamido carbonyl group and the arginineresidue at position 152 of the receptor site. In addition, the C-2 carboxyl group of sialic acid binds to Arg 118, Arg 292, andArg 371. Position C-6 is capable of undergoing a hydrophobicinteraction with various amino acids, including Glu, Ala,Arg, and Ile. Maximum binding to neuraminidase occurswhen the C-6 substituent is substituted with a nonpolar chain.In oseltamivir, this nonpolar group is 3-pentyl. An importantfeature of oseltamivir is the ethyl ester, which makes the drugorally efficacious. This drug is the first orally active agent foruse against influenza A and B. It is also indicated for the treatmentof acute illness. If administered within 2 days after theonset of influenza symptoms, the drug is effective.

제조 및 합성 방법

제조 방법

Oseltamivir phosphate (Tamiflu) has been synthesized from cis-2,3-bis(hydroxymethyl)aziridine. After protection of the cis-2,3-bis(hydroxymethyl)aziridine with a Boc group, desymmetrization provided a chiral aziridine, which was a key intermediate to install the required stereogenic center containing a nitrogen atom. Allylation and ring closing metathesis are the key reactions to obtain the cyclic product that was successfully converted to the desired oseltamivir phosphate. DOI: 10.1021/jo3015853It can also be obtained by a novel 12-step synthesis from (-)-quinic acid.