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Chemistry

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Also known as: Chymotrypsin substrate i, colorimetric, 9004-07-3, 4-[[2-[[2-[[1-(4-nitroanilino)-1-oxo-3-phenylpropan-2-yl]amino]-2-oxoethyl]amino]-2-oxoethyl]amino]-4-oxobutanoic acid, A-chymotrypsin, Dtxsid30988741, Akos024350585
Molecular Formula
C23H25N5O8
Molecular Weight
499.5  g/mol
InChI Key
CFYIUBWVKZQDOG-UHFFFAOYSA-N

Chymotrypsin
A serine endopeptidase secreted by the pancreas as its zymogen, CHYMOTRYPSINOGEN and carried in the pancreatic juice to the duodenum where it is activated by TRYPSIN. It selectively cleaves aromatic amino acids on the carboxyl side.
1 2D Structure

Chymotrypsin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-[[2-[[2-[[1-(4-nitroanilino)-1-oxo-3-phenylpropan-2-yl]amino]-2-oxoethyl]amino]-2-oxoethyl]amino]-4-oxobutanoic acid
2.1.2 InChI
InChI=1S/C23H25N5O8/c29-19(10-11-22(32)33)24-13-20(30)25-14-21(31)27-18(12-15-4-2-1-3-5-15)23(34)26-16-6-8-17(9-7-16)28(35)36/h1-9,18H,10-14H2,(H,24,29)(H,25,30)(H,26,34)(H,27,31)(H,32,33)
2.1.3 InChI Key
CFYIUBWVKZQDOG-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C(C=C1)CC(C(=O)NC2=CC=C(C=C2)[N+](=O)[O-])NC(=O)CNC(=O)CNC(=O)CCC(=O)O
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Alpha-chymotrypsin Choay

2. Alphacutane

3. Avazyme

2.2.2 Depositor-Supplied Synonyms

1. Chymotrypsin Substrate I, Colorimetric

2. 9004-07-3

3. 4-[[2-[[2-[[1-(4-nitroanilino)-1-oxo-3-phenylpropan-2-yl]amino]-2-oxoethyl]amino]-2-oxoethyl]amino]-4-oxobutanoic Acid

4. A-chymotrypsin

5. Dtxsid30988741

6. Akos024350585

7. Db-055212

8. Ft-0641215

9. N-succinyl-gly-gly-phe-p-nitroanilide, Protease Substrate

10. N-(3-carboxy-1-oxopropyl)glycylglycyl-n-(4-nitrophenyl)-l-phenylalaninamide

11. 4-hydroxy-4-({2-hydroxy-2-[(2-hydroxy-2-{[1-(4-nitroanilino)-1-oxo-3-phenylpropan-2-yl]imino}ethyl)imino]ethyl}imino)butanoic Acid

2.2.3 Other Synonyms

1. Alpha Chymotrypsin

2.3 Create Date
2005-09-13
3 Chemical and Physical Properties
Molecular Weight 499.5 g/mol
Molecular Formula C23H25N5O8
XLogP30.4
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count8
Rotatable Bond Count12
Exact Mass499.17031277 g/mol
Monoisotopic Mass499.17031277 g/mol
Topological Polar Surface Area200 Ų
Heavy Atom Count36
Formal Charge0
Complexity801
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

EXPTL USE (MEDICATION (VET):): CHYMOTRYPSIN CAN BE SHOWN TO HAVE AN ANTI-INFLAMMATORY ACTION IN EXPTL ANIMALS, BUT ONLY WHEN THE ENZYME IS ADMIN PARENTERALLY IN DOSES 10 TO 20 TIMES THOSE EMPLOYED CLINICALLY & PRIOR TO THE PRODN OF THE INFLAMMATION.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 957


...USED FOR RELIEF OF SYMPTOMS RELATED TO EPISIOTOMY. ITS USEFULNESS IN INFLAMMATORY STATES SECONDARY TO SURGICAL OR PHYSICAL TRAUMA REMAINS UNPROVEN.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 957


ALPHA-CHYMOTRYPSIN...IS...USED IN CATARACT OPERATIONS TO LOOSEN THE LENS AFTER INCISION OF CORNEA. AFTER THE CORNEOSCLERAL OR CORNEOSCLERALCONJUNCTIVAL INCISION, THE POSTERIOR CHAMBER IS IRRIGATED WITH ABOUT 2 ML OF ENZYME SOLN (150 UNITS PER ML) TO FRAGMENT FIBERS OF THE ZONULE (ENZYMATIC ZONULOLYSIS).

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 957


...FOR DEBRIDEMENT OF NECROTIC WOUNDS, ULCERS, ABSCESSES, EMPYEMAS, & FISTULAS. IT HAS BEEN USED ALSO FOR LIQUIFACTION OF BLOOD & EXUDATES THAT HAVE NOT BECOME ORGANIZED BY FIBROUS TISSUE.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 972


For more Therapeutic Uses (Complete) data for CHYMOTRYPSIN (10 total), please visit the HSDB record page.


4.2 Drug Warning

...IT IS NOT RECOMMENDED FOR USE IN OPHTHALMIC SURGERY IN PT UNDER 20 YEARS OF AGE BECAUSE OF POSSIBLE LOSS OF VITREOUS HUMOR.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 957


GLAUCOMA, AS A COMPLICATION OF USE OF CHYMOTRYPSIN IN CATARACT EXTRACTIONS IN PT, HAS OCCURED USUALLY WITHIN 2 TO 5 DAYS AFTER OPERATION... THERE HAVE BEEN PRACTICALLY NO INDICATIONS OF LONGER-PERSISTING GLAUCOMA, FROM USE OF THE ENZYME.

Grant, W. M. Toxicology of the Eye. 2nd ed. Springfield, Illinois: Charles C. Thomas, 1974., p. 292


4.3 Drug Indication

No therapeutic indications.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Chymotrypsin is a digestive enzyme synthesized in the pancreas that plays an essential role in proteolysis, or the breakdown of proteins and polypeptides. As a component in the pancreatic juice, chymotrypsin aids in the digestion of proteins in the duodenum by preferentially cleaving peptide amide bonds.


5.2 ATC Code

B - Blood and blood forming organs

B06 - Other hematological agents

B06A - Other hematological agents

B06AA - Enzymes

B06AA04 - Chymotrypsin


S - Sensory organs

S01 - Ophthalmologicals

S01K - Surgical aids

S01KX - Other surgical aids

S01KX01 - Chymotrypsin


5.3 Absorption, Distribution and Excretion

Absorption

No pharmacokinetic data available.


Route of Elimination

No pharmacokinetic data available.


Volume of Distribution

No pharmacokinetic data available.


Clearance

No pharmacokinetic data available.


5.4 Metabolism/Metabolites

No pharmacokinetic data available.


5.5 Biological Half-Life

No pharmacokinetic data available.


5.6 Mechanism of Action

Chymotrypsin is synthesized by pancreatic acinar cells as an inactive precursor, chymotrypsinogen, that is secreted to the duodenum and activated via trypsin-induced cleavage. It also induces its own activation by cleaving essential amino acid residues in the oxyanion hole to produce -Chymotrypsin, which is a more stable form than -Chymotrypsin. Residues His-57, Asp-102, and Ser-195 form the catalytic triad while residues 189195, 214220, and 225228 form the primary substrate-binding pocket called S1 binding pocket. Residue 189 in the polar serine residue that lies at the bottom of the S1 binding pocket. Chymotrypsin favors aromatic residues like phenylalanine, tyrosine, and tryptophan but may hydrolyze other bonds in peptides at slower rates.


THEY SPLIT SECONDARY AMIDE OR PEPTIDE BONDS, CARBOXYLIC OR PHENOLIC ESTER BONDS & EVEN CARBON-CARBON BONDS. THEIR MAIN FUNCTION IS TO HYDROLYZE PEPTIDE BONDS DURING THE INTESTINAL DIGESTION OF PROTEINS. /CHYMOTRYPSINS/

The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 293


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24-May-2022
24-May-2022
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