Oseltamivir phosphate

한글명:Oseltamivir phosphate

카스 번호204255-11-8

상품명:Oseltamivir phosphate

CBNumberCB2119221

분자식C16H31N2O8P

포뮬러 무게410.4

MOL 파일204255-11-8.mol

화학적 성질

녹는점	196-198°C
저장 조건	2-8°C
용해도	H2O: 가용성30mg/mL, 투명
물리적 상태	가루
색상	흰색에서 베이지색
optical activity	[α]/D -26 to -36°, c = 1 in H2O
수용성	Soluble in water (75 mM)
BCS Class	1 (CLogP), 3 (LogP)
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)19;1-5(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\|
CAS 데이터베이스	204255-11-8(CAS DataBase Reference)

위험 및 안전 성명

위험 등급

IRRITANT

HS 번호

2924299500

NFPA 704:

	0
2		0

그림문자(GHS)

Oseltamivir phosphate 화학적 특성, 용도, 생산

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.
화학적 성질
White Cyrstalline Solid. It is freely soluble in water.
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
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/jo3015853

It can also be obtained by a novel 12-step synthesis from (-)-quinic acid.
정의
ChEBI: Oseltamivir phosphate is a phosphate salt. It contains an oseltamivir. It is an acetamido cyclohexene that is a structural homolog of SIALIC ACID and inhibits NEURAMINIDASE.
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.
Clinical Use
Oseltamivir was approved as the first orally administered neuraminidase inhibitor used against influenza A and B viruses. The drug is indicated for the treatment of uncomplicated acute illness caused by influenza infection.
부작용
Side effects with oseltamivir are minor, consist of nausea and vomiting, and occur primarily in the first two days of therapy.
신진 대사
Oseltamivir is readily absorbed from the GI tract following oral administration. It is a prodrug that is extensively metabolized in the liver, undergoing ester hydrolysis to the active carboxylic acid. Two oxidative metabolites also have been isolated, with the major oxidation product being the ω-carboxylic acid.
Mode of action
Oseltamivir Phosphate is the phosphate salt of oseltamivir, a synthetic derivative prodrug of ethyl ester with antiviral activity. By blocking neuraminidases on the surfaces of influenza viruses, oseltamivir interferes with host cell release of complete viral particles.

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