| Identification | Back Directory | [Name]
TIROFIBAN HYDROCHLORIDE MONOHYDRATE | [CAS]
142373-60-2 | [Synonyms]
butoxy)
L 700462
Tirofiban Hydrochloride
TirofibanhydrochlorideHCl
-3-(4-(4-(piperidin-4-yl)
Tirofiban hydrochloride 1-hydrate
Tirofiban hydrochloride monohydrate Tirofiban Hydrochloride
N-(Butylsulfonyl)-O-[4-(4-piperidinyl)butyl]-L-tyrosine hydrochloride
N-(Butylsulfonyl)-o-(4-(4-piperidinyl)butyl)-L-tyrosine monohydrochloride
2-(butylsulfonaMido)-3-(4-(4-(piperidin-4-yl)butoxy)phenyl)propanoic acid
L-Tyrosine, N-(butylsulfonyl)-o-(4-(4-piperidinyl)butyl)-, monohydrochloride
L-Tyrosine,N-(butylsulfonyl)-O-[4-(4-piperidinyl)butyl]-, hydrochloride (1:1)
(S)-2-(Butylsulfonamido)-3-(4-(4-(piperidin-4-yl)butoxy)phenyl)propanoic acid
2-(butylsulfonylamino)-3-[4-[4-(4-piperidinyl)butoxy]phenyl]propanoic acid hydrochloride
(S)-2-(Butylsulfonamido)-3-(4-(4-(piperidin-4-yl)butoxy)phenyl)propanoic acid hydrochloride | [Molecular Formula]
C22H39ClN2O6S | [MDL Number]
MFCD07368623 | [MOL File]
142373-60-2.mol | [Molecular Weight]
495.07 |
| Chemical Properties | Back Directory | [Melting point ]
83-87oC | [solubility ]
Methanol (Slightly) | [form ]
Solid | [color ]
White | [InChI]
InChI=1/C22H36N2O5S.ClH.H2O/c1-2-3-16-30(27,28)24-21(22(25)26)17-19-7-9-20(10-8-19)29-15-5-4-6-18-11-13-23-14-12-18;;/h7-10,18,21,23-24H,2-6,11-17H2,1H3,(H,25,26);1H;1H2/t21-;;/s3 | [InChIKey]
HWAAPJPFZPHHBC-MGIYCFTINA-N | [SMILES]
S(CCCC)(=O)(=O)N[C@@H](CC1=CC=C(C=C1)OCCCCC1CCNCC1)C(O)=O.Cl.O |&1:8,r| | [CAS DataBase Reference]
142373-60-2 |
| Hazard Information | Back Directory | [Description]
Tirofiban was launched as Aggrastat in Switzerland and the US for
patients with unstable angina or non-Q-wave myocardial infarction to prevent
cardiac ischemic events. Tirofiban is synthesized from (S)-tyrosine by a fourstep
process. Tirofiban is a novel highly potent antiplatelet agent that inhibits the
interaction of fibrinogen with GPⅡb/Ⅲa, an activated platelet membrane-bound
glycoprotein complex. It prevents arterial thrombus formation in a dosedependent
manner. Clinical efficacy was highly significant with an absolute and
relative risk reduction. In these studies, treatment with tirofiban was well
tolerated, without significant adverse effects. | [Originator]
Sibutramine (Sibutramine) | [Uses]
Aggrastat (Millot
Laboratories, France). | [Manufacturing Process]
The synthesis of tirofiban starts by reaction of tyrosine with bis-trimethylsilyl
trifluoraceramide to give a derivative in which both functions -OH and COOH_x0002_are protected. Treatment of this intermediate with butylsulfonyl chloride gives
the corresponding sulfonamide derivative; the quite labile silyl groups are then
removed under mildly acidic conditions to give N-butylsulfonyl-tyrosine. In a
parallel scheme, 4-picoline is converted to its anion by means of butyl lithium;
this gives 4-(4-chlorobutyl)-pyridine on alkylation with 1-bromo-3-
chloropropane. The reaction of this compound with N-butylsulfonyl-tyrosine in
presence of NaOH gives the ether 2-butylsulfonyaminol-3-[4-pyridin-4-ylbutoxy-phenyl]propionic acid. Hydrogenation over palladium on charcoal then
reduce the pyridine ring to a piperidine to afford the fibrinogen receptor
antagonist tirofiban. | [Brand name]
Tirofiban is INN and BAN. | [Therapeutic Function]
Fibrinogen receptor antagonist |
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