PROLINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C5H9NO2
Molecular Weight	115.1305
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)[C@@H]1CCCN1

InChI

InChIKey=ONIBWKKTOPOVIA-BYPYZUCNSA-N

InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C5H9NO2
Molecular Weight	115.1305
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugbank.ca/drugs/DB00172 | https://www.ema.europa.eu/en/documents/scientific-guideline/draft-information-package-leaflet-regarding-proline-used-excipient-medicinal-products-human-use_en.pdf

Proline (L-Proline) is one of the twenty amino acids used in living organisms as the building blocks of proteins. Proline is a non-essential amino acid that is synthesized from glutamic acid. It is an essential component of collagen and is important for proper functioning of joints and tendons. Proline is used in pharmaceuticals as an excipient and as an active substance in nutritional supplements. Proline is not commonly used in pharmaceuticals as an excipient. It is approved for use in Privigen (IVIg) and Hizentra (SCIg) solution for injection as a stabiliser for IgG. Proline is also contained in low amounts in several vaccines, e.g. Havrix 720 Kinder (Hepatitis A).

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Proline dehydrogenase 1, mitochondrial 4 Target ID: O43272\|\|\|Q9UF13 Gene ID: 5625.0 Gene Symbol: PRODH Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16874462	Substrate 661
OH radicals 4 Target ID: OH radicals Sources: https://www.ncbi.nlm.nih.gov/pubmed/24328335	Binding Agent 1064
Proton-coupled amino acid transporter 2 4 Target ID: Q495M3 Gene ID: 153201.0 Gene Symbol: SLC36A2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22711289	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Burns 17 Sources: https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=016822	Primary		Approved 8429	FREAMINE III 10% Approved Use Parenteral nutrition with 8.5% FreAmine® III (Amino Acid Injection) with Electrolytes is indicated to prevent nitrogen loss or treat negative nitrogen balance in adults and pediatric patients, where (1) the alimentary tract, by the oral, gastrostomy, or jejunostomy route, cannot or should not be used, or adequate protein intake is not feasible by these routes; (2) gastrointestinal absorption of protein is impaired; or (3) protein requirements are substantially increased as with extensive burns. Dosage, route of administration, and concomitant infusion of non-protein calories are dependent on various factors, such as nutritional metabolic status of the patient, anticipated duration of parenteral nutritional support, and vein tolerance Launch Date 5.4345601E10

PubMed

Title	Date	PubMed
Proline dipeptidase from Pyrococcus furiosus.	2001	11210522
Development and characterization of tissue-engineered aortic valves.	2001 Feb	11224920
Antifreeze glycoproteins: relationship between molecular weight, thermal hysteresis and the inhibition of leakage from liposomes during thermotropic phase transition.	2001 Feb	11207440
The mGlu(2/3) agonist 2R,4R-4-aminopyrrolidine-2,4-dicarboxylate, is anti- and proconvulsant in DBA/2 mice.	2001 Feb 16	11166954
Cbl-b, a RING-type E3 ubiquitin ligase, targets phosphatidylinositol 3-kinase for ubiquitination in T cells.	2001 Feb 16	11087752
Cloning of dopamine, norepinephrine and serotonin transporters from monkey brain: relevance to cocaine sensitivity.	2001 Feb 19	11223167
A single nucleotide polymorphic mutation in the human mu-opioid receptor severely impairs receptor signaling.	2001 Feb 2	11067846
DNA recognition by the methyl-CpG binding domain of MeCP2.	2001 Feb 2	11035019
Different susceptibility to oxidation of proline and arginine residues of apolipoprotein B-100 among subspecies of low density lipoproteins.	2001 Feb 23	11226433
Polymorphism of TP53 codon 72 and the risk of cervical cancer among Korean women.	2001 Jan	11174479
Secretion monitor, SecM, undergoes self-translation arrest in the cytosol.	2001 Jan	11172723
Proline transport in MDCK cells expressing a mutant regulatory subunit of cAMP-dependent protein kinase.	2001 Jan	11161828
Mutated-gamma-actin restores growth to a yeast amino acid transport defective mutant.	2001 Jan	11147807
Regulatory role of arginase I and II in nitric oxide, polyamine, and proline syntheses in endothelial cells.	2001 Jan	11120661
Analysis of collagenase-cleavage of type II collagen using a neoepitope ELISA.	2001 Jan 1	11150534
The destabilization of human GCAP1 by a proline to leucine mutation might cause cone-rod dystrophy.	2001 Jan 1	11136713
Antioxidant therapy attenuates JNK activation and apoptosis in the remote noninfarcted myocardium after large myocardial infarction.	2001 Jan 12	11162522
p13(SUC1) and the WW domain of PIN1 bind to the same phosphothreonine-proline epitope.	2001 Jan 12	11013245
Cloning and functional expression of rat kidney dipeptidyl peptidase II.	2001 Jan 15	11139392
Short, solubilized polyalanines are conformational chameleons: exceptionally helical if N- and C-capped with helix stabilizers, weakly to moderately helical if capped with rigid spacers.	2001 Jan 16	11148022
Implication of a small GTPase Rac1 in the activation of c-Jun N-terminal kinase and heat shock factor in response to heat shock.	2001 Jan 19	11050083
Structural basis for oligosaccharide recognition by Pyrococcus furiosus maltodextrin-binding protein.	2001 Jan 26	11162100
The mechanism for anthracycline-induced inhibition of collagen biosynthesis.	2001 Jan 5	11137854
Mutation of proline 409 to arginine in the meander region of cytochrome p450c17 causes severe 17 alpha-hydroxylase deficiency.	2001 Mar	11243732
Crystallization and characterization of the prolidase from Pyrococcus furiosus.	2001 Mar	11223522
Arginine and ornithine kinetics in severely burned patients: increased rate of arginine disposal.	2001 Mar	11171607
Effects of Doxorubicin (Adriamycin) and [(+)-1,2-bis(3,5-dioxopiperazinyl-1-yl)]propane (ICRF-187) on skeletal muscle protease activities.	2001 Mar 15	11243912
Novel gene mutations in patients with left ventricular noncompaction or Barth syndrome.	2001 Mar 6	11238270

Patents

Sample Use Guides

In Vivo Use Guide

As an active substance proline is used as an oral nutritional supplement in OTC supplements by a 97 number of companies in doses ranging from 500 mg/d to 1000 mg/d and in numerous amino acid 98 mixtures intended for parenteral nutrition such as 10% FreAmine® III, B. Braun Medical Inc.

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:02:01 UTC 2023` Edited by `admin` on `Fri Dec 15 15:02:01 UTC 2023`
Record UNII	9DLQ4CIU6V
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PROLINE

Official Name

English

PROLINE [USAN]

Common Name

English

PROLINE [II]

Common Name

English

L-PROLINE [JAN]

Common Name

English

PROLINE [USP MONOGRAPH]

Common Name

English

PROLINE [MART.]

Common Name

English

Proline [WHO-DD]

Common Name

English

L-PROLINE [FCC]

Common Name

English

L-2-PYRROLIDINECARBOXYLIC ACID

Common Name

English

FEMA NO. 3319

Code

English

PROLINE [HSDB]

Common Name

English

L-PROLINE

Systematic Name

English

PROLINE [INCI]

Common Name

English

NSC-46703

Code

English

PROLINE [VANDF]

Common Name

English

L-PROLINE [USP-RS]

Common Name

English

proline [INN]

Common Name

English

PROLINE [EP MONOGRAPH]

Common Name

English

L-PROLINE [FHFI]

Common Name

English

PROLINE [MI]

Common Name

English

Classification Tree Code System Code

LOINC

25510-9