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Basic Information

Molecular Structure:
CAS No.:	128270-60-0
Name:	Bivalirudin
Article Data:	11

Formula:	C₉₈H₁₃₈N₂₄O₃₃
Molecular Weight:	2180.31
Synonyms:	L-Leucine,D-phenylalanyl-L-prolyl-L-arginyl-L-prolylglycylglycylglycylglycyl-L-asparaginylglycyl-L-a-aspartyl-L-phenylalanyl-L-a-glutamyl-L-a-glutamyl-L-isoleucyl-L-prolyl-L-a-glutamyl-L-a-glutamyl-L-tyrosyl-;126:PN: WO2004076484 PAGE: 31 claimed protein;Angiomax;BG 8967;Hirulog;Hirulog 1;Bivalirudin Trifluoroacetate;
Density:	1.52 g/cm³
Appearance:	White powder
PSA:	901.57000
LogP:	0.54320

Synthetic route

: Boc-D-Phe-Pro-Arg(Pbf)-Pro-Gly-Gly-Gly-Gly-Asn(Trt)-Gly-Asp(tBu)-Phe-Glu(tBu)-Glu(tBu)-Ile-Pro-Glu(tBu)-Glu(tBu)-Tyr(tBu)-Leu-OtBu

: 128270-60-0
bivalirudin

Conditions

Conditions	Yield
With water; trifluoroacetic acid; 1-dodecylthiol at 20℃; for 1h; Reagent/catalyst;	110 g

: 21691-53-2
L-leucine tert-butyl ester

: 29022-11-5
N-(fluoren-9-ylmethoxycarbonyl)glycine

: Fmoc-Arg(Pbf)-OH

: H-Asp-(tBu)

: 112883-29-1, 92954-90-0
N-Fmoc-Tyr-OH

: 18942-49-9
Boc-D-Phe-OH

: 71989-31-6
Fmoc-Pro-OH

: 71989-18-9
Fmoc-Glu(OtBu)-OH

: 71989-23-6
Fmoc-Ile-OH

: 132388-59-1
L-Asn(Trt)

: 128270-60-0
bivalirudin

Conditions

Conditions	Yield
Stage #1: L-leucine tert-butyl ester; N-Fmoc-Tyr-OH With benzotriazol-1-ol; diisopropyl-carbodiimide In 1-methyl-pyrrolidin-2-one; dichloromethane at 0 - 30℃; Stage #2: With piperidine In 1-methyl-pyrrolidin-2-one Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Arg(Pbf)-OH; H-Asp-(tBu); Boc-D-Phe-OH; Fmoc-Pro-OH; Fmoc-Glu(OtBu)-OH; Fmoc-Ile-OH; L-Asn(Trt) Further stages;

...Expand

Boc-D-Phe-Pro-Arg(Pbf)-Pro-Gly-Gly-Gly-Gly-Asn(Trt)-Gly-Asp(OtBu)-Phe-Glu(OtBu)-Glu(OtBu)-Ile-Pro-Glu(OtBu)-Glu(OtBu)-Tyr(tBu)-Leu-O(benzyl(3,4,5-tridihydrophtyloxy)): Boc-D-Phe-Pro-Arg(Pbf)-Pro-Gly-Gly-Gly-Gly-Asn(Trt)-Gly-Asp(OtBu)-Phe-Glu(OtBu)-Glu(OtBu)-Ile-Pro-Glu(OtBu)-Glu(OtBu)-Tyr(tBu)-Leu-O(benzyl(3,4,5-tridihydrophtyloxy))

: 128270-60-0
bivalirudin

Conditions

Conditions	Yield
With chlorotriisopropylsilane; trifluoroacetic acid In water at 20℃; for 3h; Cooling with ice;

: 29022-11-5
N-(fluoren-9-ylmethoxycarbonyl)glycine

: 35661-60-0
Fmoc-Leu-OH

: 71989-31-6
Fmoc-Pro-OH

: 35661-40-6
N-Fmoc L-Phe

: 71989-14-5
Fmoc-(tBu)Asp-OH

: 71989-18-9
Fmoc-Glu(OtBu)-OH

: 71989-23-6
Fmoc-Ile-OH

: 71989-38-3
Fmoc-Tyr(tBu)-OH

: 132388-59-1
L-Asn(Trt)

Fmoc-D-Phe-OH: Fmoc-D-Phe-OH

: Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine

: 128270-60-0
bivalirudin

Conditions

Conditions	Yield
Stage #1: Fmoc-Leu-OH With N-ethyl-N,N-diisopropylamine at 90℃; for 0.0833333h; Automated synthesizer; Stage #2: With pyrrolidine at 95℃; for 0.0138889h; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Pro-OH; N-Fmoc L-Phe; Fmoc-(tBu)Asp-OH; Fmoc-Glu(OtBu)-OH; Fmoc-Ile-OH; Fmoc-Tyr(tBu)-OH; L-Asn(Trt); Fmoc-D-Phe-OH; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine Further stages;

Yield

Stage #1: Fmoc-Leu-OH With N-ethyl-N,N-diisopropylamine at 90℃; for 0.0833333h; Automated synthesizer;
Stage #2: With pyrrolidine at 95℃; for 0.0138889h;
Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Pro-OH; N-Fmoc L-Phe; Fmoc-(tBu)Asp-OH; Fmoc-Glu(OtBu)-OH; Fmoc-Ile-OH; Fmoc-Tyr(tBu)-OH; L-Asn(Trt); Fmoc-D-Phe-OH; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine Further stages;

...Expand

HCl*H-D-Phe-Pro-Arg(Pbf)-Pro-Gly-Gly-Gly-Gly-Asn(Trt)-Gly-Asp(OtBu)-Phe-Glu(OtBu)-Glu(OtBu)-Ile-Pro-Glu(OtBu)-Glu(OtBu)-Tyr(tBu)-Leu-OKb, Kb=2,4-didocosyloxybenzyl: HCl*H-D-Phe-Pro-Arg(Pbf)-Pro-Gly-Gly-Gly-Gly-Asn(Trt)-Gly-Asp(OtBu)-Phe-Glu(OtBu)-Glu(OtBu)-Ile-Pro-Glu(OtBu)-Glu(OtBu)-Tyr(tBu)-Leu-OKb, Kb=2,4-didocosyloxybenzyl

: 128270-60-0
bivalirudin

Conditions

Conditions	Yield
With chlorotriisopropylsilane; water; trifluoroacetic acid at 20℃; for 3h;

Total:219 Page 1 of 6 1 2 3 4 5 6 Next>>

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Specification

1. Introduction of Bivalirudin
Bivalirudin is one kind of white powder or off-white powder. The IUPAC Name of it is (15S,21S,24S,27S,30S)-15-(2-Amino-2-oxoethyl)-1-[(2S)-1-{(2S)-2-[({(2S)-1-[(2R)-2-amino-3-phenylpropanoyl]pyrrolidin-2-yl} carbonyl)amino]-5-carbamimidamidopentanoyl}pyrrolidin-2-yl]-24-benzyl-30-({(2S,3S)-1-[(2S)-2 -{[(2S)-4-carboxy-1-{[(2S)-4-carboxy-1-{[(2S)-1-{[(1S)-1-carboxy-3-methylbutyl]amino}-3 -(4-hydroxyphenyl)-1-oxopropan-2-yl]amino}-1-oxobutan-2-yl]amino}-1-oxobutan-2-yl]carbamoyl}pyrroli\ndin -1-yl]-3-methyl-1-oxopentan-2-yl}carbamoyl)-27-(2-carboxyethyl)-21-(carboxymethyl)-1,4,7,10,13,16,19,22, 25,28-decaoxo-2,5,8,11,14,17,20,23,26,29-decaazatritriacontan-33-oic acid.

It is belongs to Peptide. The Classification Code of Bivalirudin is Anticoagulant; Anticoagulants; Antithrombins; Antithrombotic; Enzyme Inhibitors; Hematologic Agents; Protease Inhibitors; Serine Proteinase Inhibitors. Bivalirudin is readily soluble in water and freely filtered at the glomerulus.

2. Properties of Bivalirudin
Physical properties about Bivalirudin are:
(1)Density: 1.52 g/cm³; (2)Freely Rotating Bonds: 68; (3)Polar Surface Area: 901.57 Å²; (4)Index of Refraction: 1.674; (5)Molar Refractivity: 537.76 cm³; (6)Molar Volume: 1431.3 cm³; (7)Surface Tension: 69.5 dyne/cm.

3. Structure Descriptors of Bivalirudin
(1)InChI: InChI=1S/C98H138N24O33/c1-5-52(4)82(96(153)122-39-15-23-70(122)92(149)114-60(30-34-79(134)135)85(142)111-59(29-33-78(132)133)86(143)116-64(43-55-24-26-56(123)27-25-55)89(146)118-67(97(154)155)40-51(2)3)119-87(144)61(31-35-80(136)137)112-84(141)58(28-32-77(130)131)113-88(145)63(42-54-18-10-7-11-19-54)117-90(147)66(45-81(138)139)110-76(129)50-107-83(140)65(44-71(100)124)109-75(128)49-106-73(126)47-104-72(125)46-105-74(127)48-108-91(148)68-21-13-38-121(68)95(152)62(20-12-36-103-98(101)102)115-93(150)69-22-14-37-120(69)94(151)57(99)41-53-16-8-6-9-17-53/h6-11,16-19,24-27,51-52,57-70,82,123H,5,12-15,20-23,28-50,99H2,1-4H3,(H2,100,124)(H,104,125)(H,105,127)(H,106,126)(H,107,140)(H,108,148)(H,109,128)(H,110,129)(H,111,142)(H,112,141)(H,113,145)(H,114,149)(H,115,150)(H,116,143)(H,117,147)(H,118,146)(H,119,144)(H,130,131)(H,132,133)(H,134,135)(H,136,137)(H,138,139)(H,154,155)(H4,101,102,103)/t52-,57+,58-,59-,60-,61-,62-,63-,64-,65-,66-,67-,68-,69-,70-,82-/m0/s1
(2)InChIKey: InChIKey=OIRCOABEOLEUMC-GEJPAHFPSA-N
(3)Smiles: C([C@H]1N(CCC1)C([C@@H](Cc1ccccc1)N)=O)(=O)N[C@H](C(N1[C@H](C(=O)NCC(=O)NCC(NCC(=O)NCC(=O)N[C@H](C(NCC(=O)N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(=O)N2[C@@H](CCC2)C(=O)N[C@H](C(N[C@H](C(N[C@@H](Cc2ccc(O)cc2)C(N[C@@H](CC(C)C)C(=O)O)=O)=O)CCC(O)=O)=O)CCC(O)=O)[C@H](CC)C)=O)CCC(O)=O)=O)CCC(O)=O)=O)Cc2ccccc2)=O)CC(O)=O)=O)CC(=O)N)=O)CCC1)=O)CCCNC(N)=N

4. Uses of Bivalirudin
Bivalirudin (CAS NO.128270-60-0) is a specific and reversible direct thrombin inhibitor (DTI). Chemically, it is a synthetic congener of the naturally occurring drug hirudin (found in the saliva of the medicinal leech Hirudo medicinalis). It is a DTI which overcomes many limitations seen with indirect thrombin inhibitors, such as heparin. Bivalirudin is used as alternative medicine to unfractionated heparin and platelet glycoprotein IIb / IIIa antagonist. Bivalirudin is an anticoagulant.

Bivalirudin is intended for IV use only and is supplied as a sterile, lyophilized product in single-use, glass vials. After reconstitution, each vial delivers 250 mg of bivalirudin. Bivalirudin clinical studies demonstrated consistent positive outcomes in patients with stable angina, unstable angina (UA), non-ST segment elevation myocardial infarction (NSTEMI), and ST-segment elevation myocardial infarction (STEMI) undergoing PCI in 7 major randomized trials.