NAV

Antipain

Identification

Generic Name
Antipain
DrugBank Accession Number
DB15251
Background

Antipain is a serine/cysteine protease inhibitor originally isolated from various strains of actinomycetes.1 Early studies investigated the potential for antipain to alter DNA damage and chromosomal aberrations in irradiated cells or those treated with chemical mutagens such as N-methyl-N'-nitro-N-nitrosoguanidine (MNNG).2,3

Antipain was used in 2010 to obtain a crystal structure of the Leishmania major oligopeptidase B (OPB), a serine protease that serves as a virulence factor in trypanosomatids.4 The binding of antipain to OPB has been used in molecular dynamic studies to identify other OPB inhibitors with more favourable pharmacodynamic and pharmacokinetic properties for potential development as anti-trypanosomatid drugs.5,6

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 604.713
Monoisotopic: 604.344529177
Chemical Formula
C27H44N10O6
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
47V479BE6L
CAS number
37691-11-5
InChI Key
SDNYTAYICBFYFH-TUFLPTIASA-N
InChI
InChI=1S/C27H44N10O6/c1-16(2)21(23(40)34-18(15-38)10-6-12-32-25(28)29)37-22(39)19(11-7-13-33-26(30)31)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,(H,34,40)(H,37,39)(H,41,42)(H4,28,29,32)(H4,30,31,33)(H2,35,36,43)/t18-,19-,20-,21-/m0/s1
IUPAC Name
(2S)-2-({[(1S)-4-carbamimidamido-1-{[(1S)-1-{[(2S)-5-carbamimidamido-1-oxopentan-2-yl]carbamoyl}-2-methylpropyl]carbamoyl}butyl]carbamoyl}amino)-3-phenylpropanoic acid
SMILES
CC(C)[C@H](NC(=O)[C@H](CCCNC(N)=N)NC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C=O

References

General References
  1. Suda H, Aoyagi T, Hamada M, Takeuchi T, Umezawa H: Antipain, a new protease inhibitor isolated from actinomycetes. J Antibiot (Tokyo). 1972 Apr;25(4):263-6. doi: 10.7164/antibiotics.25.263. [Article]
  2. 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. doi: 10.1093/carcin/10.7.1193. [Article]
  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. doi: 10.1016/s0027-5107(98)00081-5. [Article]
  4. McLuskey K, Paterson NG, Bland ND, Isaacs NW, Mottram JC: Crystal structure of Leishmania major oligopeptidase B gives insight into the enzymatic properties of a trypanosomatid virulence factor. J Biol Chem. 2010 Dec 10;285(50):39249-59. doi: 10.1074/jbc.M110.156679. Epub 2010 Oct 5. [Article]
  5. Sodero AC, Dos Santos AC, Mello JF, DE Jesus JB, DE Souza AM, Rodrigues MI, DE Simone SG, Rodrigues CR, DE Matos Guedes HL: Oligopeptidase B and B2: comparative modelling and virtual screening as searching tools for new antileishmanial compounds. Parasitology. 2017 Apr;144(4):536-545. doi: 10.1017/S0031182016002237. Epub 2016 Dec 29. [Article]
  6. da Silva E Silva JV, Cordovil Brigido HP, Oliveira de Albuquerque KC, Miranda Carvalho J, Ferreira Reis J, Vinhal Faria L, Coelho-Ferreira M, Silveira FT, da Silva Carneiro A, Percario S, do Rosario Marinho AM, Dolabela MF: Flavopereirine-An Alkaloid Derived from Geissospermum vellosii-Presents Leishmanicidal Activity In Vitro. Molecules. 2019 Feb 21;24(4). pii: molecules24040785. doi: 10.3390/molecules24040785. [Article]
ChemSpider
34678
ChEMBL
CHEMBL1230912
ZINC
ZINC000008716755
Wikipedia
Antipain

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0835 mg/mLALOGPS
logP-0.73ALOGPS
logP-3.4Chemaxon
logS-3.9ALOGPS
pKa (Strongest Acidic)3.42Chemaxon
pKa (Strongest Basic)12.05Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count12Chemaxon
Hydrogen Donor Count11Chemaxon
Polar Surface Area277.5 Å2Chemaxon
Rotatable Bond Count19Chemaxon
Refractivity178.23 m3·mol-1Chemaxon
Polarizability63.74 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pbi-0019265000-9479deb096b91ebc8dcf
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0w2j-1504793000-d330c4985ab5b46faa77
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03mr-2931640000-b0617e8820c31dccf714
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01pc-1312890000-e0deae2eb8a63341a570
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03fr-0922100000-8ebc44c9d108ad4071a4
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ox-7916100000-7888736e245215605399
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Drug created at May 20, 2019 15:04 / Updated at June 24, 2020 01:34