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MedKoo Cat#: 598080 | Name: Antipain free base

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Antipain is a reversible, cell-permeable oligopeptide protease inhibitor primarily targeting serine and cysteine proteases, including trypsin, papain, and cathepsins A, B, and L. It exhibits IC₅₀ values in the low micromolar to nanomolar range—approximately 2 µM for trypsin and as low as 100 nM for cathepsin B. Antipain also inhibits the proteasome’s chymotrypsin-like activity, though with moderate potency. It has been shown to protect cells from apoptosis in certain contexts by preventing proteolytic degradation of key intracellular substrates. Due to its specificity and low toxicity in vitro, antipain is widely used in biochemical studies to dissect protease function and in assays requiring preservation of native protein integrity.

Chemical Structure

Antipain free base
Antipain free base
CAS#37691-11-5 (free base)

Theoretical Analysis

MedKoo Cat#: 598080

Name: Antipain free base

CAS#: 37691-11-5 (free base)

Chemical Formula: C27H44N10O6

Exact Mass: 604.3445

Molecular Weight: 604.71

Elemental Analysis: C, 53.63; H, 7.33; N, 23.16; O, 15.87

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Related CAS #
37691-11-5 (free base) 37682-72-7 (HCl)
Synonym
Antipain; CCRIS 3605;
IUPAC/Chemical Name
(((2S)-1-(((S)-1-amino-3-methyl-1-oxobutan-2-yl)(5-guanidino-1-oxopentan-2-yl)amino)-5-guanidino-1-oxopentan-2-yl)carbamoyl)phenylalanine
InChi Key
JDJDCTHSLWTHBU-MAHYXTOZSA-N
InChi Code
InChI=1S/C27H44N10O6/c1-16(2)21(22(28)39)37(18(15-38)10-6-12-33-25(29)30)23(40)19(11-7-13-34-26(31)32)35-27(43)36-20(24(41)42)14-17-8-4-3-5-9-17/h3-5,8-9,15-16,18-21H,6-7,10-14H2,1-2H3,(H2,28,39)(H,41,42)(H4,29,30,33)(H4,31,32,34)(H2,35,36,43)/t18?,19-,20?,21-/m0/s1
SMILES Code
CC(C)[C@@H](C(N)=O)N(C([C@H](CCCNC(N)=N)NC(NC(C(O)=O)CC1=CC=CC=C1)=O)=O)C(C=O)CCCNC(N)=N
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 604.71 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Nakae K, Kojima F, Sawa R, Kubota Y, Igarashi M, Kinoshita N, Adachi H, Nishimura Y, Akamatsu Y. Antipain Y, a new antipain analog that inhibits neurotransmitter release from rat dorsal root ganglion neurons. J Antibiot (Tokyo). 2010 Jan;63(1):41-4. doi: 10.1038/ja.2009.109. Epub 2009 Nov 13. PubMed PMID: 19911027. 2: DiPaolo JA, Amsbaugh SC, Popescu NC. Antipain inhibits N-methyl-N'-nitro-N-nitrosoguanidine-induced transformation and increases chromosomal aberrations. Proc Natl Acad Sci U S A. 1980 Nov;77(11):6649-53. PubMed PMID: 6935676; PubMed Central PMCID: PMC350344. 3: Afzal V, Wiencke JK, Wolff S. Antipain-mediated suppression of X-ray-induced chromosomal aberrations in human lymphocytes. Carcinogenesis. 1989 Jul;10(7):1193-6. PubMed PMID: 2736713. 4: Ichikawa-Ryo H, Kondo S. Differential antimutagenic effects of caffeine and the protease inhibitor antipain on mutagenesis by various mutagens in Escherichia coli. Mutat Res. 1980 Sep;72(2):311-22. PubMed PMID: 7003368. 5: Isogai E, Suzuki N. Involvement of antipain-sensitive protease activity in suppression of UV-mutagenicity by human interferon-alpha. Mutat Res. 1994 Nov;325(2-3):81-5. PubMed PMID: 7523935. 6: Sugita K, Suzuki N, Niimi H. Involvement of antipain-sensitive protease activity in the interferon-beta-induced UV-refractoriness of Cockayne syndrome fibroblasts. Mutat Res. 1996 Oct 25;357(1-2):177-81. PubMed PMID: 8876692. 7: Nguyen QV, Knapp W, Humphreys RE. Inhibition by leupeptin and antipain of the intracellular proteolysis of Ii. Hum Immunol. 1989 Mar;24(3):153-63. PubMed PMID: 2925452. 8: Sun C, Colman M, Redpath JL. Suppression of the radiation-induced expression of a tumor-associated antigen in human cell hybrids by the protease inhibitor antipain. Carcinogenesis. 1988 Dec;9(12):2333-5. PubMed PMID: 3191580. 9: Zagorul'ko OI, Gnezdilov AV, Medvedeva LA, Samoĭlova NV. [The necessity and possibilities of the antipain help organization in multyprofile clinics]. Khirurgiia (Mosk). 2013;(1):13-6. Review. Russian. PubMed PMID: 23503344. 10: Coombs GH, Baxter J. Inhibition of Leishmania amastigote growth by antipain and leupeptin. Ann Trop Med Parasitol. 1984 Feb;78(1):21-4. PubMed PMID: 6721611. 11: Schwartz JL, Weichselbaum RR. Antipain-mediated suppression of sister chromatid exchanges induced by an inhibitor of poly (ADP-ribose) polymerase. Environ Mutagen. 1985;7(5):703-9. PubMed PMID: 3930238. 12: Nomura T, Enomoto T, Shibata K, Kanzaki T, Tanaka H, Hata S, Kimura S, Kusafuka T, Sobue K, Miyamoto S, et al. Antiteratogenic effects of tumor inhibitors, caffeine, antipain, and retinoic acid in mice. Cancer Res. 1983 Nov;43(11):5156-62. PubMed PMID: 6413055. 13: Bolli R, Cannon RO, Speir E, Goldstein RE, Epstein SE. Role of cellular proteinases in acute myocardial infarction. I. Proteolysis in nonischemic and ischemic rat myocardium and the effects of antipain, leupeptin, pepstatin and chymostatin administered in vivo. J Am Coll Cardiol. 1983 Oct;2(4):671-80. PubMed PMID: 6350399. 14: Long SD, Quigley JP, Troll W, Kennedy AR. Protease inhibitor antipain suppresses 12-O-tetradecanoyl-phorbol-13-acetate induction of plasminogen activator in transformable mouse embryo fibroblasts. Carcinogenesis. 1981;2(9):933-6. PubMed PMID: 6794928. 15: Picard A, Labbé JC, Peaucellier G, Dorée M. Antipain microinjection prevents progesterone to inhibit adenyl cyclase in Xenopus oocytes. Cell Biol Int Rep. 1987 Feb;11(2):81-8. PubMed PMID: 2435416. 16: Vaccari M, Argnani A, Horn W, Silingardi P, Giungi M, Mascolo MG, Bartoli S, Grilli S, Colacci A. Effects of the protease inhibitor antipain on cell malignant transformation. Anticancer Res. 1999 Jan-Feb;19(1A):589-96. PubMed PMID: 10226603. 17: Ruggiero M, Lapetina EG. Antipain or leupeptin in combination with aspirin or indomethacin synergistically inhibit human platelet activation by thrombin and trypsin. Adv Prostaglandin Thromboxane Leukot Res. 1987;17A:563-8. PubMed PMID: 2959114. 18: Isogai E, Ishijima S, Sonoda T, Kita K, Suzuki H, Hasegawa R, Yamamori H, Takakubo Y, Suzuki N. Protease activation following UV irradiation is linked to hypomutability in human cells selected for resistance to combination of UV and antipain. Mutat Res. 1998 Jul 17;403(1-2):215-22. PubMed PMID: 9726021. 19: Nomura T, Hata S, Enomoto T, Tanaka H, Shibata K. Inhibiting effects of antipain on urethane-induced lung neoplasia in mice. Br J Cancer. 1980 Oct;42(4):624-6. PubMed PMID: 7437293; PubMed Central PMCID: PMC2010431. 20: Suzuki K, Tsuji S, Ishiura S. Effect of Ca2+ on the inhibition of calcium-activated neutral protease by leupeptin, antipain and epoxysuccinate derivatives. FEBS Lett. 1981 Dec 21;136(1):119-22. PubMed PMID: 6274695.