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Lepirudin

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Lepirudin is an anticoagulant that acts as a direct thrombin inhibitor. Lepirudin binds to both free and clot-bound thrombin. Lepirudin is approved for the treatment of heparin-induced thrombocytopenia (HIT).

Category

Peptide Inhibitors

Catalog number

BAT-010047

CAS number

138068-37-8

Molecular Formula

C287H440N80O111S6

Molecular Weight

6979.41

Size	Price	Stock	Quantity
1 mg	$839	In stock

Specification
Reference Reading

IUPAC Name

(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2S,3R)-2-[[2-[[(2S)-2-[[2-[[(2S,3R)-2-[[(2S)-2-[[(1R,6R,9S,12S,15S,18S,24S,27S,33S,36S,39R,44R,47S,53S,56S,59S,67S,73S,76S)-15,76-bis(4-aminobutyl)-44-[[(2S)-2-[[(4R,7S,10S,13S,19S,22S,25S,28R)-28-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-hydroxybutanoyl]amino]-3-carboxypropanoyl]amino]-10-(2-amino-2-oxoethyl)-13-(3-amino-3-oxopropyl)-22-(2-carboxyethyl)-25-[(1R)-1-hydroxyethyl]-19-(hydroxymethyl)-7-(2-methylpropyl)-6,9,12,15,18,21,24,27-octaoxo-1,2-dithia-5,8,11,14,17,20,23,26-octazacyclononacosane-4-carbonyl]amino]-4-methylpentanoyl]amino]-12,56,73-tris(2-amino-2-oxoethyl)-9,67-bis(3-amino-3-oxopropyl)-36-[(2S)-butan-2-yl]-18,47-bis(2-carboxyethyl)-24-(carboxymethyl)-27,53-bis(hydroxymethyl)-33-(2-methylpropyl)-8,11,14,17,20,23,26,29,32,35,38,45,48,51,54,57,60,62,65,68,71,74,77-tricosaoxo-59-propan-2-yl-3,4,41,42-tetrathia-7,10,13,16,19,22,25,28,31,34,37,46,49,52,55,58,61,63,66,69,72,75,78-tricosazabicyclo[37.22.17]octaheptacontane-6-carbonyl]amino]-3-methylbutanoyl]amino]-3-hydroxybutanoyl]amino]acetyl]amino]-4-carboxybutanoyl]amino]acetyl]amino]-3-hydroxybutanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-hydroxypropanoyl]amino]-3-(1H-imidazol-4-yl)propanoyl]amino]-4-oxobutanoyl]amino]-3-carboxypropanoyl]amino]acetyl]amino]-3-carboxypropanoyl]amino]-3-phenylpropanoyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbonyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-methylpentanoyl]amino]-5-oxopentanoic acid

Synonyms

(Leu1,Thr2)-Hirudin (desulfated); Lepirudin; Refludan; Refludin; Hbw 023; Hbw-023; Hbw023

Melting Point

65°C

Sequence

LTYTDCTESGQNLCLCEGSNVCGQGNKCILGSDGEKNQCVTGEGTPKPQSHNDGDFEEIPEEYLQ

InChI

InChI=1S/C287H440N80O111S6/c1-24-132(17)225-280(470)345-162(87-126(5)6)236(426)306-111-209(396)320-181(116-370)267(457)344-176(101-220(416)417)238(428)307-105-203(390)316-152(61-74-213(402)403)243(433)321-146(40-29-32-80-288)241(431)339-171(96-198(298)385)259(449)326-153(56-69-194(294)381)250(440)351-186(121-482-479-118-183-240(430)310-107-202(389)313-148(54-67-192(292)379)233(423)303-108-206(393)317-170(95-197(297)384)258(448)322-147(41-30-33-81-289)242(432)350-187(272(462)359-225)122-483-480-119-184(269(459)323-150(60-73-212(400)401)235(425)304-110-208(395)319-180(115-369)266(456)342-174(99-201(301)388)265(455)357-223(130(13)14)278(468)355-183)352-254(444)165(90-129(11)12)335-270(460)185-120-481-484-123-188(354-263(453)178(103-222(420)421)347-283(473)230(137(22)375)362-264(454)168(93-141-48-52-144(378)53-49-141)346-282(472)228(135(20)373)361-232(422)145(291)86-125(3)4)273(463)363-229(136(21)374)281(471)330-158(65-78-217(410)411)249(439)348-179(114-368)239(429)309-106-204(391)315-151(55-68-193(293)380)244(434)340-172(97-199(299)386)260(450)334-164(89-128(9)10)253(443)353-185)271(461)358-224(131(15)16)279(469)364-227(134(19)372)277(467)311-112-205(392)314-149(59-72-211(398)399)234(424)305-113-210(397)356-231(138(23)376)286(476)367-85-37-45-191(367)276(466)331-160(42-31-34-82-290)284(474)365-83-35-43-189(365)274(464)328-154(57-70-195(295)382)248(438)349-182(117-371)268(458)338-169(94-142-104-302-124-312-142)257(447)341-173(98-200(300)387)261(451)343-175(100-219(414)415)237(427)308-109-207(394)318-177(102-221(418)419)262(452)337-166(91-139-38-27-26-28-39-139)255(445)327-155(62-75-214(404)405)245(435)325-159(66-79-218(412)413)251(441)360-226(133(18)25-2)285(475)366-84-36-44-190(366)275(465)329-157(64-77-216(408)409)246(436)324-156(63-76-215(406)407)247(437)336-167(92-140-46-50-143(377)51-47-140)256(446)333-163(88-127(7)8)252(442)332-161(287(477)478)58-71-196(296)383/h26-28,38-39,46-53,104,124-138,145-191,223-231,368-378H,24-25,29-37,40-45,54-103,105-123,288-291H2,1-23H3,(H2,292,379)(H2,293,380)(H2,294,381)(H2,295,382)(H2,296,383)(H2,297,384)(H2,298,385)(H2,299,386)(H2,300,387)(H2,301,388)(H,302,312)(H,303,423)(H,304,425)(H,305,424)(H,306,426)(H,307,428)(H,308,427)(H,309,429)(H,310,430)(H,311,467)(H,313,389)(H,314,392)(H,315,391)(H,316,390)(H,317,393)(H,318,394)(H,319,395)(H,320,396)(H,321,433)(H,322,448)(H,323,459)(H,324,436)(H,325,435)(H,326,449)(H,327,445)(H,328,464)(H,329,465)(H,330,471)(H,331,466)(H,332,442)(H,333,446)(H,334,450)(H,335,460)(H,336,437)(H,337,452)(H,338,458)(H,339,431)(H,340,434)(H,341,447)(H,342,456)(H,343,451)(H,344,457)(H,345,470)(H,346,472)(H,347,473)(H,348,439)(H,349,438)(H,350,432)(H,351,440)(H,352,444)(H,353,443)(H,354,453)(H,355,468)(H,356,397)(H,357,455)(H,358,461)(H,359,462)(H,360,441)(H,361,422)(H,362,454)(H,363,463)(H,364,469)(H,398,399)(H,400,401)(H,402,403)(H,404,405)(H,406,407)(H,408,409)(H,410,411)(H,412,413)(H,414,415)(H,416,417)(H,418,419)(H,420,421)(H,477,478)/t132-,133-,134+,135+,136+,137+,138+,145-,146-,147-,148-,149-,150-,151-,152-,153-,154-,155-,156-,157-,158-,159-,160-,161-,162-,163-,164-,165-,166-,167-,168-,169-,170-,171-,172-,173-,174-,175-,176-,177-,178-,179-,180-,181-,182-,183-,184-,185-,186-,187-,188-,189-,190-,191-,223-,224-,225-,226-,227-,228-,229-,230-,231-/m0/s1

InChI Key

FIBJDTSHOUXTKV-BRHMIFOHSA-N

Canonical SMILES

CCC(C)C1C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(CSSCC2C(=O)NCC(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(CSSCC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)N2)C(C)C)CC(=O)N)CO)CCC(=O)O)NC(=O)C(CC(C)C)NC(=O)C3CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)N3)CC(C)C)CC(=O)N)CCC(=O)N)CO)CCC(=O)O)C(C)O)NC(=O)C(CC(=O)O)NC(=O)C(C(C)O)NC(=O)C(CC4=CC=C(C=C4)O)NC(=O)C(C(C)O)NC(=O)C(CC(C)C)N)C(=O)N1)CCCCN)CC(=O)N)CCC(=O)N)C(=O)NC(C(C)C)C(=O)NC(C(C)O)C(=O)NCC(=O)NC(CCC(=O)O)C(=O)NCC(=O)NC(C(C)O)C(=O)N5CCCC5C(=O)NC(CCCCN)C(=O)N6CCCC6C(=O)NC(CCC(=O)N)C(=O)NC(CO)C(=O)NC(CC7=CNC=N7)C(=O)NC(CC(=O)N)C(=O)NC(CC(=O)O)C(=O)NCC(=O)NC(CC(=O)O)C(=O)NC(CC8=CC=CC=C8)C(=O)NC(CCC(=O)O)C(=O)NC(CCC(=O)O)C(=O)NC(C(C)CC)C(=O)N9CCCC9C(=O)NC(CCC(=O)O)C(=O)NC(CCC(=O)O)C(=O)NC(CC1=CC=C(C=C1)O)C(=O)NC(CC(C)C)C(=O)NC(CCC(=O)N)C(=O)O)CCC(=O)N)CC(=O)N)CCCCN)CCC(=O)O)CC(=O)O)CO)CC(C)C

1. Lepirudin in the management of patients with heparin-induced thrombocytopenia

Sirak Petros Biologics . 2008 Sep;2(3):481-90. doi: 10.2147/btt.s3415.

Lepirudin, a recombinant hirudin, is a direct irreversible thrombin inhibitor by binding to both free and clot-bound thrombin. It is approved for treatment of heparin-induced thrombocytopenia (HIT), which is a serious antibody-mediated drug reaction mostly associated with the use of unfractionated heparin. Clinical experience during the last 10 years has proved the efficacy of lepirudin in the management of HIT. The major route of elimination of lepirudin is the kidney, accounting for approximately 90% of its systemic clearance. The most important adverse reactions are bleeding and the induction of immunologic reactions. The risk of bleeding can be reduced by implementing an optimal monitoring and dose adjustment strategy, particularly in patients undergoing cardiopulmonary bypass surgery and in those with impaired renal function. Development of antihirudin antibodies may enhance the anticoagulant effect of lepirudin. Anaphylactic reactions associated with lepirudin therapy are rare. The lack of an antidote against lepirudin is still a concern, particularly during cardiopulmonary bypass surgery with a heart-lung machine and during artificial renal support. Currently, hemofiltration using high-flux filter systems is the only available and valid means to manage hirudin overdose. Nevertheless, the drug can be safely used if meticulous monitoring strategy is installed.

2. Lepirudin: a bivalent direct thrombin inhibitor for anticoagulation therapy

Andreas Greinacher Expert Rev Cardiovasc Ther . 2004 May;2(3):339-57. doi: 10.1586/14779072.2.3.339.

Lepirudin (Refludan), Berlex Laboratories, USA and Canada; Pharmion, all other countries), a recombinant derivative of the naturally occurring leech anticoagulant hirudin, was the first direct thrombin inhibitor to be approved by the European Agency for the Evaluation of Medicinal Products and the US Food and Drug Administration for the treatment of heparin-induced thrombocytopenia. Since its introduction into Europe and the USA, it has been studied in over 7000 patients requiring anticoagulation in conditions including acute coronary syndromes, percutaneous coronary intervention, cardiopulmonary bypass and heparin-induced thrombocytopenia. Three European clinical trials, designated Heparin-Associated Thrombocytopenia (HAT)-1, -2 and -3, demonstrated the efficacy and safety of lepirudin in the prevention and treatment of thrombosis in patients with antibody-confirmed heparin-induced thrombocytopenia. A postmarketing, observational study, termed the Drug-Monitoring Program, evaluated lepirudin in over 1000 patients with heparin-induced thrombocytopenia in the setting of routine clinical practice. In the Drug-Monitoring Program, adverse events were substantially reduced compared with clinical trials, while clinical efficacy was maintained; suggesting that insight gained through clinical experience was translated into improved safety. Here, pharmacotherapy using lepirudin is reviewed, with particular reference to clinical studies in heparin-induced thrombocytopenia, and some recommendations based on this extensive clinical experience with lepirudin are provided. Although only approved for the treatment of heparin-induced thrombocytopenia, the use of lepirudin in acute coronary syndromes, percutaneous coronary intervention, vascular surgery and coronary artery bypass grafting is also discussed. The review concludes with a discussion of pharmacokinetic and clinical data supporting the potential for subcutaneous administration of lepirudin.

3. Lepirudin

Lepirudin is no longer marketed in the United States. Limited information indicates that lepirudin in doses up to 100 mg daily produce very low levels in milk. Because of its large molecular weight, it would not be expected to be absorbed from breastmilk by the infant. Lepirudin would not be expected to cause any adverse effects in breastfed infants, especially if the infant is older than 2 months.[1]