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Substance Name: Aprotinin [USAN:USP:INN:BAN]
RN: 9087-70-1
UNII: 04XPW8C0FL
InChIKey: ZPNFWUPYTFPOJU-LPYSRVMUSA-N

Note

  • A single-chain polypeptide derived from bovine tissues consisting of 58 amino-acid residues. It is an inhibitor of proteolytic enzymes including CHYMOTRYPSIN; KALLIKREIN; PLASMIN; and TRYPSIN. It is used in the treatment of HEMORRHAGE associated with raised plasma concentrations of plasmin. It is also used to reduce blood loss and transfusion requirements in patients at high risk of major blood loss during and following open heart surgery with EXTRACORPOREAL CIRCULATION. (Reynolds JEF(Ed): Martindale: The Extra Pharmacopoeia (electronic version). Micromedex, Inc, Englewood, CO, 1995)

Molecular Formula

  • C284-H432-N84-O79-S7

Molecular Weight

  • 6511.5078
 

Classification Codes

  • Coagulants
  • Enzyme Inhibitor (Proteinase)
  • Enzyme Inhibitors
  • Hematologic Agents
  • Hemostatics
  • Protease Inhibitors
  • Reproductive Effect
  • Serine Proteinase Inhibitors
  • Trypsin Inhibitors

Names and Synonyms

Name of Substance

  • Aprotinin
  • Aprotinin [USAN:USP:INN:BAN]

MeSH Heading

  • Aprotinin

Synonyms

  • Antagosan
  • Antikrein
  • Antilysin
  • Antilysine
  • Aprotinin
  • Aprotinin bovine
  • Aprotinin solution
  • Aprotinina
  • Aprotinina [INN-Spanish]
  • Aprotinine
  • Aprotinine [INN-French]
  • Aprotininum
  • Aprotininum [INN-Latin]
  • Basic pancreatic trypsin inhibitor
  • Basic protease inhibitor
  • BAYA0128
  • Bayer A 128
  • BPTI
  • Contrykal
  • EINECS 232-994-9
  • Fosten
  • Gordox
  • HSDB 7502
  • Inhibin
  • Iniprol
  • Kallikrein-trypsin inactivator
  • Kir richter
  • Kunitz and Northrop inhibitor
  • L-Arginyl-L-prolyl-L-aspartyl-L-phenylalanyl-L-cysteinyl-L-leucyl-L-glutamyl-L-prolyl-L-prolyl-L-tyrosyl-L-threonylglycyl-L-prolyl-L-cysteinyl-L-lysyl-L-alanyl-L-arginyl-L-isoleucyl-L-isoleucyl-L-arginyl-L-tyrosyl-L-phenylalanyl-L-tyrosyl-L-asparaginyl-L-alanyl-L-lysyl-L-alanylglycyl-L-leucyl-L-cysteinyl-L-glutaminyl-L-threonyl-L-phenylalanyl-L-valyl-L-tyrosylglycylglycyl-L-cysteinyl-L-arginyl-L-alanyl-L-lysyl-L-arginyl-L-asparaginyl-L-asparaginyl-L-phenylalanyl-L-lysyl-L-seryl-L-alanyl-L-glutamyl-L-aspartyl-L-cysteinyl-L-methionyl-L-arginyl-L-threonyl-L-cysteinylglycylglycyl-L-alanine cyclic (5-55), (14-38), (30-51) tris(disulfide)
  • Onquinin
  • Pancreatic basic trypsin inhibitor
  • Pancreatic trypsin inhibitor
  • Pancreatic trypsin inhibitor (kunitz)
  • Pantinol
  • Protimbin
  • Repulson
  • Riker 52G
  • RP 9921
  • RP-9921
  • Trascolan
  • Trasylol
  • Trazinin
  • Trypsin inhibitor
  • Trypsin-kallikrein inhibitor (kunitz)
  • Tzalol
  • UNII-04XPW8C0FL
  • Zymofren

Systematic Name

  • Trypsin inhibitor, pancreatic basic

Registry Numbers

CAS Registry Number

  • 9087-70-1

FDA UNII

  • 04XPW8C0FL

Other Registry Numbers

  • 11005-72-4
  • 11132-77-7
  • 39283-52-8
  • 69431-34-1
  • 9004-04-0
  • 9039-77-4

System Generated Number

  • 0009087701

Structure Descriptors

InChI

InChI=1S/C284H432N84O79S7/c1-21-144(9)222-271(439)337-174(68-46-105-309-282(300)301)239(407)340-187(120-160-77-85-164(374)86-78-160)251(419)341-185(116-156-55-29-24-30-56-156)250(418)342-188(121-161-79-87-165(375)88-80-161)252(420)346-191(123-208(291)378)246(414)322-149(14)230(398)326-168(62-35-39-98-285)234(402)319-146(11)227(395)314-132-215(385)324-181(113-141(3)4)247(415)354-199-137-452-453-138-200-263(431)336-179(97-112-448-20)242(410)331-176(70-48-107-311-284(304)305)244(412)363-226(154(19)372)274(442)358-197(233(401)316-129-212(382)312-130-213(383)318-151(16)278(446)447)135-449-451-139-201(355-253(421)186(117-157-57-31-25-32-58-157)344-256(424)195(127-220(393)394)350-267(435)204-72-50-109-366(204)275(443)167(289)61-43-102-306-279(294)295)265(433)339-182(114-142(5)6)248(416)338-180(93-96-218(389)390)276(444)368-111-52-74-206(368)277(445)367-110-51-73-205(367)268(436)349-189(122-162-81-89-166(376)90-82-162)259(427)362-224(152(17)370)269(437)317-133-216(386)365-108-49-71-203(365)266(434)357-202(264(432)333-169(63-36-40-99-286)235(403)320-148(13)229(397)328-175(69-47-106-310-283(302)303)243(411)360-223(145(10)22-2)272(440)361-222)140-454-450-136-198(325-214(384)131-313-211(381)128-315-232(400)183(119-159-75-83-163(373)84-76-159)351-270(438)221(143(7)8)359-258(426)190(118-158-59-33-26-34-60-158)352-273(441)225(153(18)371)364-245(413)177(335-262(199)430)91-94-207(290)377)261(429)334-172(66-44-103-307-280(296)297)236(404)321-147(12)228(396)327-170(64-37-41-100-287)237(405)330-173(67-45-104-308-281(298)299)238(406)345-192(124-209(292)379)255(423)347-193(125-210(293)380)254(422)343-184(115-155-53-27-23-28-54-155)249(417)332-171(65-38-42-101-288)240(408)353-196(134-369)260(428)323-150(15)231(399)329-178(92-95-217(387)388)241(409)348-194(126-219(391)392)257(425)356-200/h23-34,53-60,75-90,141-154,167-206,221-226,369-376H,21-22,35-52,61-74,91-140,285-289H2,1-20H3,(H2,290,377)(H2,291,378)(H2,292,379)(H2,293,380)(H,312,382)(H,313,381)(H,314,395)(H,315,400)(H,316,401)(H,317,437)(H,318,383)(H,319,402)(H,320,403)(H,321,404)(H,322,414)(H,323,428)(H,324,385)(H,325,384)(H,326,398)(H,327,396)(H,328,397)(H,329,399)(H,330,405)(H,331,410)(H,332,417)(H,333,432)(H,334,429)(H,335,430)(H,336,431)(H,337,439)(H,338,416)(H,339,433)(H,340,407)(H,341,419)(H,342,418)(H,343,422)(H,344,424)(H,345,406)(H,346,420)(H,347,423)(H,348,409)(H,349,436)(H,350,435)(H,351,438)(H,352,441)(H,353,408)(H,354,415)(H,355,421)(H,356,425)(H,357,434)(H,358,442)(H,359,426)(H,360,411)(H,361,440)(H,362,427)(H,363,412)(H,364,413)(H,387,388)(H,389,390)(H,391,392)(H,393,394)(H,446,447)(H4,294,295,306)(H4,296,297,307)(H4,298,299,308)(H4,300,301,309)(H4,302,303,310)(H4,304,305,311)/t144-,145-,146-,147-,148-,149-,150-,151-,152+,153+,154+,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-,192-,193-,194-,195-,196-,197-,198-,199-,200-,201-,202-,203-,204-,205-,206-,221-,222-,223-,224-,225-,226-/m0/s1

InChIKey

ZPNFWUPYTFPOJU-LPYSRVMUSA-N

Smiles

CC[C@H](C)[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](C)NC(=O)[C@H](CCCCN)NC(=O)[C@@H]2CSSC[C@@H]3NC(=O)CNC(=O)CNC(=O)[C@H](Cc4ccc(O)cc4)NC(=O)[C@@H](NC(=O)[C@H](Cc5ccccc5)NC(=O)[C@@H](NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CSSC[C@H](NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](Cc6ccccc6)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(=N)N)NC3=O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](Cc7ccccc7)NC(=O)[C@H](CC(=O)O)NC(=O)[C@@H]8CCCN8C(=O)[C@@H](N)CCCNC(=N)N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N9CCC[C@H]9C(=O)N%10CCC[C@H]%10C(=O)N[C@@H](Cc%11ccc(O)cc%11)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N%12CCC[C@H]%12C(=O)N2)C(=O)NCC(=O)NCC(=O)N[C@@H](C)C(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](Cc%13ccc(O)cc%13)NC(=O)[C@H](Cc%14ccccc%14)NC(=O)[C@H](Cc%15ccc(O)cc%15)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](NC1=O)[C@@H](C)CC)[C@@H](C)O)C(C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal > 50mL/kg (50mL/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Oyo Yakuri. Pharmacometrics. Vol. 28, Pg. 329, 1984.
mouse LD50 subcutaneous > 50mL/kg (50mL/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Oyo Yakuri. Pharmacometrics. Vol. 28, Pg. 329, 1984.
rat LD50 intraperitoneal > 40mL/kg (40mL/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Oyo Yakuri. Pharmacometrics. Vol. 28, Pg. 329, 1984.
rat LD50 subcutaneous > 40mL/kg (40mL/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Oyo Yakuri. Pharmacometrics. Vol. 28, Pg. 329, 1984.