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MedKoo Cat#: 540023 | Name: Antipain HCl
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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 HCl
Antipain HCl
CAS#37682-72-7 (HCl)

Theoretical Analysis

MedKoo Cat#: 540023

Name: Antipain HCl

CAS#: 37682-72-7 (HCl)

Chemical Formula: C27H45ClN10O6

Exact Mass: 0.0000

Molecular Weight: 641.17

Elemental Analysis: C, 50.58; H, 7.07; Cl, 5.53; N, 21.85; O, 14.97

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
25mg USD 750.00 2 Weeks
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Related CAS #
37691-11-5 (free base) 37682-72-7 (HCl)
Synonym
BDBM32804 HCl; BDBM-32804 HCl; BDBM 32804 HCl, Antipain HCl
IUPAC/Chemical Name
N2-[[[(1S)-1-carboxy-2-phenylethyl]amino]carbonyl]-L-arginyl-N-[4-[(aminoiminomethyl)amino]-1-formylbutyl]-L-valinamide, dihydrochloride
InChi Key
GIIPXDJELXIITN-PKGYLJHQSA-N
InChi Code
InChI=1S/C27H44N10O6.2ClH/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);2*1H/t18?,19-,20-,21-;;/m0../s1
SMILES Code
CC(C)[C@@H](C(N)=O)N(C([C@H](CCCNC(N)=N)NC(N[C@H](C(O)=O)CC1=CC=CC=C1)=O)=O)C(C=O)CCCNC(N)=N.[H]Cl.[H]Cl
Appearance
Solid powder
Purity
>95% (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
>2 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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 641.17 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: Aguda AH, Lavallee V, Cheng P, Bott TM, Meimetis LG, Law S, Nguyen NT, Williams DE, Kaleta J, Villanueva I, Davies J, Andersen RJ, Brayer GD, Brömme D. Affinity Crystallography: A New Approach to Extracting High-Affinity Enzyme Inhibitors from Natural Extracts. J Nat Prod. 2016 Aug 26;79(8):1962-70. doi: 10.1021/acs.jnatprod.6b00215. Epub 2016 Aug 6. PubMed PMID: 27498895. 3: 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. 4: Souza-Silva F, Bourguignon SC, Pereira BA, Côrtes LM, de Oliveira LF, Henriques-Pons A, Finkelstein LC, Ferreira VF, Carneiro PF, de Pinho RT, Caffarena ER, Alves CR. Epoxy-α-lapachone has in vitro and in vivo anti-leishmania (Leishmania) amazonensis effects and inhibits serine proteinase activity in this parasite. Antimicrob Agents Chemother. 2015 Apr;59(4):1910-8. doi: 10.1128/AAC.04742-14. Epub 2015 Jan 12. PubMed PMID: 25583728; PubMed Central PMCID: PMC4356828. 5: 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. 6: Hockensmith K, Dillard K, Sanders B, Harville BA. Identification and characterization of a chymotrypsin-like serine protease from periodontal pathogen, Tannerella forsythia. Microb Pathog. 2016 Nov;100:37-42. doi: 10.1016/j.micpath.2016.08.041. Epub 2016 Sep 1. PubMed PMID: 27594668. 7: Tolbert MK, Brand MD, Gould EN. In vitro effects of cysteine protease inhibitors on Trichomonas foetus-induced cytopathic changes in porcine intestinal epithelial cells. Am J Vet Res. 2016 Aug;77(8):890-7. doi: 10.2460/ajvr.77.8.890. PubMed PMID: 27463553. 8: Streit AK, Fan YN, Masullo L, Baines RA. Calcium Imaging of Neuronal Activity in Drosophila Can Identify Anticonvulsive Compounds. PLoS One. 2016 Feb 10;11(2):e0148461. doi: 10.1371/journal.pone.0148461. eCollection 2016. PubMed PMID: 26863447; PubMed Central PMCID: PMC4749298. 9: 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. 10: Bhunia B, Basak B, Mandal T, Bhattacharya P, Dey A. Effect of pH and temperature on stability and kinetics of novel extracellular serine alkaline protease (70 kDa). Int J Biol Macromol. 2013 Mar;54:1-8. doi: 10.1016/j.ijbiomac.2012.11.024. Epub 2012 Nov 28. PubMed PMID: 23219732. 11: 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. 12: Suzuki N. Suppression of UV- and interferon-alpha-refractoriness by antipain in human IFr cells established from RSa cells sensitive to both stimuli. J Cell Physiol. 1996 Apr;167(1):47-51. PubMed PMID: 8698839. 13: Iarygin VN, Lipkina EV, Mustafin AG. [Effect of morphine and antipain on synthesis of RNA in neurons and hepatocytes of WAG and F344 rats]. Biull Eksp Biol Med. 1998 Feb;125(2):221-3. Russian. PubMed PMID: 9559143. 14: Anisuzzaman, Islam MK, Alim MA, Miyoshi T, Hatta T, Yamaji K, Matsumoto Y, Fujisaki K, Tsuji N. Longistatin is an unconventional serine protease and induces protective immunity against tick infestation. Mol Biochem Parasitol. 2012 Mar-Apr;182(1-2):45-53. doi: 10.1016/j.molbiopara.2011.12.002. Epub 2011 Dec 21. PubMed PMID: 22206819. 15: Kadowaki T, Kitano S, Baba A, Takii R, Hashimoto M, Katunuma N, Yamamoto K. Isolation and characterization of a novel and potent inhibitor of Arg-gingipain from Streptomyces sp. strain FA-70. Biol Chem. 2003 Jun;384(6):911-20. PubMed PMID: 12887058. 16: Iwaoka M, Katakura A, Mishima J, Ishihara Y, Kunwar A, Priyadarsini KI. Mimicking the lipid peroxidation inhibitory activity of phospholipid hydroperoxide glutathione peroxidase (GPx4) by using fatty acid conjugates of a water-soluble selenolane. Molecules. 2015 Jul 7;20(7):12364-75. doi: 10.3390/molecules200712364. PubMed PMID: 26198222. 17: Kean WF, Rainsford KD, Kean IR. Management of chronic musculoskeletal pain in the elderly: opinions on oral medication use. Inflammopharmacology. 2008 Apr;16(2):53-75. doi: 10.1007/s10787-008-1623-7. Review. PubMed PMID: 18389178. 18: Takeuchi K, Sakaue T, Yamamoto Y, Nishi K, Ohkubo I. Shedding of gACE from residual body membrane of rat sperm. Leg Med (Tokyo). 2009 Apr;11 Suppl 1:S309-10. doi: 10.1016/j.legalmed.2009.02.074. Epub 2009 Apr 17. PubMed PMID: 19375970. 19: 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. 20: Ionov M, Gordiyenko NV, Zukowska I, Tokhtaeva E, Mareninova OA, Baram N, Ziyaev K, Rezhepov K, Zamaraeva M. Stability and antioxidant activity of gossypol derivative immobilized on N-polyvinylpyrrolidone. Int J Biol Macromol. 2012 Dec;51(5):908-14. doi: 10.1016/j.ijbiomac.2012.08.005. Epub 2012 Aug 10. PubMed PMID: 22910577.