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

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 1971

PubMed

Title	Date	PubMed
The first constant-domain (CH1) exon of human IGHG2 is polymorphic and in strong linkage disequilibrium with the CH2 exon polymorphism encoding the G2m(n+) allotype in Caucasians.	2001	11220626
Proline dipeptidase from Pyrococcus furiosus.	2001	11210522
Structural bases of collagen stabilization induced by proline hydroxylation.	2001 Apr 15	11241217
Recognition and stabilization of a unique CPRI--structural motif in cucurbitaceae family trypsin inhibitor peptides: molecular dynamics based homology modeling using the X-ray structure of MCTI-II.	2001 Feb	11245252
Long-term antioxidant administration attenuates mineralocorticoid hypertension and renal inflammatory response.	2001 Feb	11230373
p38 Map kinase regulates vascular smooth muscle cell collagen synthesis by angiotensin II in SHR but not in WKY.	2001 Feb	11230337
Mutation at codon 130 in hepatitis B virus (HBV) core region increases markedly during acute exacerbation of hepatitis in chronic HBV carriers.	2001 Feb	11227666
Development and characterization of tissue-engineered aortic valves.	2001 Feb	11224920
Comparison of in vitro systems of protein digestion using either mammal or fish proteolytic enzymes.	2001 Feb	11223397
Changes in free amino acids in the hemolymph of giant freshwater prawn Macrobrachium rosenbergii exposed to varying salinities: relationship to osmoregulatory ability.	2001 Feb	11223393
Antifreeze glycoproteins: relationship between molecular weight, thermal hysteresis and the inhibition of leakage from liposomes during thermotropic phase transition.	2001 Feb	11207440
Construction of phosphatidylethanolamine-less strain of Saccharomyces cerevisiae. Effect on amino acid transport.	2001 Feb	11180458
Purification, molecular cloning, and immunohistochemical localization of dipeptidyl peptidase II from the rat kidney and its identity with quiescent cell proline dipeptidase.	2001 Feb	11173530
Importance of a proline-rich sequence in the amino-terminal region for correct folding of mitochondrial and soluble microbial p450s.	2001 Feb	11173529
Microsomal p450s use specific proline-rich sequences for efficient folding, but not for maintenance of the folded structure.	2001 Feb	11173528
Identification of a new Leu354Pro mutation responsible for factor XIII deficiency.	2001 Feb	11168522
Non-alpha-helical elements modulate polytopic membrane protein architecture.	2001 Feb 16	11237604
Functions of WW domains in the nucleus.	2001 Feb 16	11223034
The mGlu(2/3) agonist 2R,4R-4-aminopyrrolidine-2,4-dicarboxylate, is anti- and proconvulsant in DBA/2 mice.	2001 Feb 16	11166954
Cloning of dopamine, norepinephrine and serotonin transporters from monkey brain: relevance to cocaine sensitivity.	2001 Feb 19	11223167
Proline-catalyzed asymmetric aldol reactions between ketones and alpha-unsubstituted aldehydes.	2001 Feb 22	11178828
Microsporidia: emerging pathogenic protists.	2001 Feb 23	11230819
Different susceptibility to oxidation of proline and arginine residues of apolipoprotein B-100 among subspecies of low density lipoproteins.	2001 Feb 23	11226433
Solution structure of Grb2 reveals extensive flexibility necessary for target recognition.	2001 Feb 23	11178911
Transforming growth factor-beta(1) stimulates L-arginine transport and metabolism in vascular smooth muscle cells: role in polyamine and collagen synthesis.	2001 Feb 27	11222476
Solution structure determination and mutational analysis of the papillomavirus E6 interacting peptide of E6AP.	2001 Feb 6	11170455
The role of a proline-induced broken-helix motif in alpha-helix 2 of Bacillus thuringiensis delta-endotoxins.	2001 Feb 9	11172813
The adaptive regulation of amino acid transport system A is associated to changes in ATA2 expression.	2001 Feb 9	11172802
Reduced hydrolysis of amelogenin may result in X-linked amelogenesis imperfecta.	2001 Jan	11223334
Autoregulation of the biosynthesis of the CcpA-like protein, PepR1, in Lactobacillus delbrueckii subsp bulgaricus.	2001 Jan	11200229
Reduction of wobble-position GC bases in Corynebacteria genes and enhancement of PCR and heterologous expression.	2001 Jan	11200224
[A case of bilateral coronal craniosynostosis with the P250R mutation in FGFR3 gene].	2001 Jan	11197897
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
Isolation and analysis of an aciclovir-resistant murine cytomegalovirus mutant.	2001 Jan	11166858
Intermolecular interactions between the SH3 domain and the proline-rich TH region of Bruton's tyrosine kinase.	2001 Jan 26	11231015
Effects of L-proline on phase I and phase II xenobiotic biotransformation capacities of rat and human hepatocytes in long-term collagen gel cultures.	2001 Jan-Feb	11178573
Mutation of proline 409 to arginine in the meander region of cytochrome p450c17 causes severe 17 alpha-hydroxylase deficiency.	2001 Mar	11243732
Differences in proliferation of the hematopoietic cell line TF-1 and cytokine production by peripheral blood leukocytes induced by 2 naturally occurring forms of human IL-3.	2001 Mar	11240952
A prion-like shift between two conformational forms of a recombinant thyrotropin receptor A-subunit module: purification and stabilization using chemical chaperones of the form reactive with Graves' autoantibodies.	2001 Mar	11238522
Inactivate the remaining p53 allele or the alternate p73? Preferential selection of the Arg72 polymorphism in cancers with recessive p53 mutants but not transdominant mutants.	2001 Mar	11238194
Isolation and characterisation of genomic and cDNA clones coding for a serine-, alanine-, and proline-rich protein of Trypanosoma cruzi.	2001 Mar	11226452
Purification, crystallization and preliminary crystallographic analysis of the periplasmic binding protein ProX from Escherichia coli.	2001 Mar	11223528
Crystallization and characterization of the prolidase from Pyrococcus furiosus.	2001 Mar	11223522
Induction of arginases I and II in cornea during herpes simplex virus infection.	2001 Mar	11172921
Arginine and ornithine kinetics in severely burned patients: increased rate of arginine disposal.	2001 Mar	11171607
SHIP's C-terminus is essential for its hydrolysis of PIP3 and inhibition of mast cell degranulation.	2001 Mar 1	11222379
Chemical C-terminal protein sequence analysis: improved sensitivity, length of degradation, proline passage, and combination with edman degradation.	2001 Mar 1	11180939
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

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