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Also known as: L-proline, 147-85-3, L-(-)-proline, (s)-pyrrolidine-2-carboxylic acid, (2s)-pyrrolidine-2-carboxylic acid, H-pro-oh
Molecular Formula
C5H9NO2
Molecular Weight
115.13  g/mol
InChI Key
ONIBWKKTOPOVIA-BYPYZUCNSA-N
FDA UNII
9DLQ4CIU6V

Proline
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.
1 2D Structure

Proline

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S)-pyrrolidine-2-carboxylic acid
2.1.2 InChI
InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1
2.1.3 InChI Key
ONIBWKKTOPOVIA-BYPYZUCNSA-N
2.1.4 Canonical SMILES
C1CC(NC1)C(=O)O
2.1.5 Isomeric SMILES
C1C[C@H](NC1)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
9DLQ4CIU6V
2.3 Synonyms
2.3.1 MeSH Synonyms

1. L Proline

2. L-proline

2.3.2 Depositor-Supplied Synonyms

1. L-proline

2. 147-85-3

3. L-(-)-proline

4. (s)-pyrrolidine-2-carboxylic Acid

5. (2s)-pyrrolidine-2-carboxylic Acid

6. H-pro-oh

7. 2-pyrrolidinecarboxylic Acid

8. (-)-proline

9. (-)-(s)-proline

10. (s)-2-pyrrolidinecarboxylic Acid

11. Prolinum

12. (-)-2-pyrrolidinecarboxylic Acid

13. L-pyrrolidine-2-carboxylic Acid

14. Prolina

15. (s)-proline

16. L-alpha-pyrrolidinecarboxylic Acid

17. L-prolin

18. Prolinum [latin]

19. Prolina [spanish]

20. Proline, L-

21. Proline (van)

22. (s)-2-carboxypyrrolidine

23. Proline [usan:inn]

24. Fema No. 3319

25. (l)-proline

26. (s)-(-)-proline

27. 2-pyrrolidinecarboxylic Acid, (s)-

28. Fema Number 3319

29. Cb 1707

30. Pro (iupac Abbreviation)

31. L-proline, Labeled With Carbon-14

32. Hsdb 1210

33. Ai3-26710

34. 9dlq4ciu6v

35. Chembl54922

36. 37159-97-0

37. 4305-67-3

38. Chebi:17203

39. Nsc-46703

40. Proline (l-proline)

41. Mfcd00064318

42. Carboxypyrrolidine

43. L-(2,3-3h)proline

44. Proline (usp)

45. (2s)-pyrrolidin-1-ium-2-carboxylate

46. Einecs 205-702-2

47. Unii-9dlq4ciu6v

48. Nsc 46703

49. 2-pyrrolidinecarboxylate

50. Racemic Proline

51. Rac-proline

52. S-proline

53. 3h-l-proline

54. L-proline;

55. (s)-prolin

56. Femanumber3319

57. H-pro

58. (2s)-proline

59. Pro-oh

60. L-proline,(s)

61. L-pro-oh

62. (-)-proline (s)-2-carboxypyrrolidine

63. L-proline (jp17)

64. Proline [vandf]

65. Proline [hsdb]

66. Proline [inci]

67. Proline [usan]

68. Proline [inn]

69. Proline [ii]

70. Proline [mi]

71. L-proline [fcc]

72. L-proline [jan]

73. Proline [mart.]

74. L-proline [fhfi]

75. Proline [who-dd]

76. Bmse000047

77. Bmse000947

78. Ec 205-702-2

79. (2s)-2-carboxypyrrolidine

80. Schembl7792

81. H-pro-2-chlorotrityl Resin

82. L-proline [usp-rs]

83. (s)-2-pyrralidinecarboxylate

84. (s)-2-pyrrolidinecarboxylate

85. (-)-2-pyrrolidinecarboxylate

86. (s)-2-pyrrolidinecarboxylicaci

87. Proline [ep Monograph]

88. (s)-(-)-prolin

89. Gtpl3314

90. (s)-2-pyrrolidinecarboxylicacid

91. Proline [usp Monograph]

92. Dtxsid5044021

93. L-proline, 99%, Fcc, Fg

94. (s)-2-pyrralidinecarboxylic Acid

95. Pyrrolidin-2-(s)-carboxylic Acid

96. Pharmakon1600-01301007

97. Zinc895360

98. (2s)-pyrrolidin-2-carbonsalphaure

99. Pyrrolidine-2-(s)-carboxylic Acid

100. Bcp25292

101. Hy-y0252

102. (s) -pyrrolidine-2-carboxylic Acid

103. L-proline, >=99.0% (nt)

104. (s)-(-)-pyrrolidine-2-carboxylate

105. Bdbm50000100

106. Ncgc00014017

107. Nsc760114

108. S5629

109. Akos010372120

110. Akos015856025

111. Ccg-214709

112. Cs-w019861

113. Db00172

114. Nsc-760114

115. (s)-(-)-pyrrolidine-2-carboxylic Acid

116. Ncgc00014017-02

117. Ncgc00014017-03

118. Ncgc00097126-01

119. Ac-11190

120. As-10803

121. L-proline, Bioultra, >=99.5% (nt)

122. Db-029981

123. L-proline, Saj Special Grade, >=99.0%

124. Am20080359

125. Bb 0242381

126. L-proline, Vetec(tm), 98.5-101.5%

127. P0481

128. L-proline, Vetec(tm) Reagent Grade, >=99%

129. C00148

130. D00035

131. L-proline, Reagentplus(r), >=99% (hplc)

132. M02947

133. P17692

134. 147p853

135. Q-201327

136. L-proline, Certified Reference Material, Tracecert(r)

137. Q20035886

138. A01b5b63-cc3d-4796-a7b4-c2de26a6fa93

139. F0001-2348

140. Proline, European Pharmacopoeia (ep) Reference Standard

141. Z1245635771

142. L-proline, United States Pharmacopeia (usp) Reference Standard

143. L-proline, Pharmaceutical Secondary Standard; Certified Reference Material

144. L-proline, From Non-animal Source, Meets Ep, Usp Testing Specifications, Suitable For Cell Culture

145. L-proline, Pharmagrade, Ajinomoto, Ep, Jp, Usp, Manufactured Under Appropriate Gmp Controls For Pharma Or Biopharmaceutical Production, Suitable For Cell Culture

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 115.13 g/mol
Molecular Formula C5H9NO2
XLogP3-2.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count1
Exact Mass115.063328530 g/mol
Monoisotopic Mass115.063328530 g/mol
Topological Polar Surface Area49.3 Ų
Heavy Atom Count8
Formal Charge0
Complexity103
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

/EXPL THER/ This study was aimed to evaluate protective and therapeutic effects of a specific mixture, containing vitamin C, lysine, proline, epigallocatechin gallate and zinc, as well as alpha-1-antitrypsin protein on lung tumorigenesis induced by benzo(a) pyrene [B(a)P] in mice. Swiss albino mice were divided into two main experiments, experiment (1) the mice were injected with 100 mg/kg B(a)P and lasted for 28 weeks, while experiment (2) the mice were injected with 8 doses each of 50 mg/kg B(a)P and lasted for 16 weeks. Each experiment (1 and 2) divided into five groups, group (I) received vehicle, group (II) received the protector mixture, group (III) received the carcinogen B(a)P, group (IV) received the protector together with the carcinogen (simultaneously) and group (V) received the carcinogen then the protector (consecutively). Total sialic acid, thiobarbituric acid reactive substances, vascular epithelial growth factor, hydroxyproline levels, as well as elastase and gelatinase activities showed significant elevation in group (III) in the two experiments comparing to control group (P < 0.001). These biochemical alterations were associated with histopathological changes. Administration of the protector in group IV and group V causes significant decrease in such parameters with improvement in histopathological alterations with improvement in histopathological alterations when compared with group III in the two experiments (P < 0.001). The present protector mixture has the ability to suppress neoplastic alteration and restore the biochemical and histopathological parameters towards normal on lung carcinogenesis induced by benzo(a) pyrene in mice. Furthermore, the present mixture have more protective rather than therapeutic action.

PMID:24174951 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3810580 Ibrahim AM et al; J Res Med Sci 18 (5): 427-34 (2013)


4.2 Drug Indication

L-Proline is extremely important for the proper functioning of joints and tendons and also helps maintain and strengthen heart muscles.


5 Pharmacology and Biochemistry
5.1 Pharmacology

L-Proline is a major amino acid found in cartilage and is important for maintaining youthful skin as well as repair of muscle, connective tissue and skin damage. It is also essential for the immune system, and for necessary balance of this formula. It is an essential component of collagen and is important for proper functioning of joints and tendons. L-Proline is extremely important for the proper functioning of joints and tendons. Helps maintain and strengthen heart muscles.


5.2 Absorption, Distribution and Excretion

L-proline is absorbed from the gastrointestinal tract. Ingested dietary protein is denatured in the stomach due to low pH. Denaturing and unfolding of the protein makes the chain susceptible to proteolysis. Up to 15% of dietary protein may be cleaved to peptides and amino acids by pepsins in the stomach. In the duodenum and small intestine digestion continues through hydrolytic enzymes (e.g. trypsin, chymotrypsins, elastase, carboxypeptidase). The resultant mixture of peptides and amino acids is then transported into the mucosal cells by specific carrier systems for amino acids and for di- and tripeptides. The products of digestion are rapidly absorbed. Like other amino acids L-proline is absorbed from ileum and distal jejeunum.

European Chemicals Agency (ECHA); Registered Substances, L-proline (CAS Number: 147-85-3) (EC Number: 205-702-2) (Last updated: December 29, 2015). Available from, as of May 25, 2016: https://echa.europa.eu/


Absorbed peptides are further hydrolyzed resulting in free amino acids which are secreted into the portal blood by specific carrier systems in the mucosal cell. Alternatively they are metabolized within the cell itself. Absorbed amino acids pass into the liver where a portion of the amino acids are used. The remainder pass through into the systemic circulation and are utilized by the peripheral tissue. L-proline is actively transported across the intestine from mucosa to serosal surface. The mechanism of absorption is that of the ion gradient. All L-amino acids are absorbed by Na+dependant, carrier mediated process. This transport is energy dependant by ATP. Plasma L-proline concentrations in normal subjects are reported to be ca. 168 uM/L +/- 60 mM/L with plasma samples collected from healthy volunteers after an overnight fast. As with most nutrients, plasma concentration of L-proline is subject to homeostasis. A number of hormones (e.g., thyroid hormone, catecholamines, and growth hormone) may affect plasma AA levels in diseases. However, in the physiologic state, their influence is probably marginal. However, there is the counter-regulatory hormone system with cortisol and glucagon which influences the blood level of amino acids involved in gluconeogenesis, such as L-proline.

European Chemicals Agency (ECHA); Registered Substances, L-proline (CAS Number: 147-85-3) (EC Number: 205-702-2) (Last updated: December 29, 2015). Available from, as of May 25, 2016: https://echa.europa.eu/


Body losses of amino acids are minimal because amino acids filtered by the kidneys are actively reabsorbed. Also cutaneous losses are negligible. Since there is no long term storage for amino acids in mammals, excess amino acids are degraded, mainly in the liver. Metabolism of amino acids involves removal of the amino group which is converted to urea and excreted in the urine. After removal of the amino group the rest of the acid is utilized as energy source or in anabolism of other endogenous substances. /Amino acids/

European Chemicals Agency (ECHA); Registered Substances, L-proline (CAS Number: 147-85-3) (EC Number: 205-702-2) (Last updated: December 29, 2015). Available from, as of May 25, 2016: https://echa.europa.eu/


5.3 Metabolism/Metabolites

Hepatic


L-proline exhibits the same metabolic pathway as several other amino acids do. Metabolism of L-proline is thus described by the entire pathway. This pathway (also known as "Ornithine and Proline Metabolism") describes the co-metabolism of arginine, ornithine, proline, citrulline and glutamate in humans. Arginine is synthesized from citrulline by the sequential action of the cytosolic enzymes argininosuccinate synthetase (ASS) and argininosuccinate lyase (ASL). Citrulline can be derived from ornithine via the catabolism of proline or glutamine/glutamate. Many of the reactions required to generate proline and glutamate from ornithine are located in the mitochondria. Proline is biosynthetically derived from glutamate and its immediate precursor, 1-pyrroline-5-carboxylate. The pathways linking arginine, glutamine, and proline are bidirectional. Thus, the net utilization or production of these amino acids is highly dependent on cell type and developmental stage. On a whole-body basis, synthesis of arginine occurs principally via the intestinal-renal axis, wherein epithelial cells of the small intestine, which produce citrulline primarily from glutamine and glutamate, collaborate with the proximal tubule cells of the kidney, which extract citrulline from the circulation and convert it to arginine, which is returned to the circulation. Consequently, impairment of small bowel or renal function can reduce endogenous arginine synthesis, thereby increasing the dietary requirement. Both proline and arginine are proteinogenic amino acids and are incorporated into proteins by prolyl-tRNA and arginyl-tRNA, which are synthesized by their respective tRNA synthetases. Arginine can also serve as a precursor for the synthesis of creatine and phopshocreatine through the intermediate guanidoacetic acid. A key component of the arginine/proline metabolic pathway is ornithine. In epithelial cells of the small intestine, ornithine is used primarily to synthesize citrulline and arginine, in liver cells surrounding the portal vein, ornithine functions primarily as an intermediate of the urea cycle, in liver cells surrounding the central vein, ornithine is used to synthesize glutamate and glutamine while in many peripheral tissues, ornithine is used for the synthesis of glutamate and proline.

European Chemicals Agency (ECHA); Registered Substances, L-proline (CAS Number: 147-85-3) (EC Number: 205-702-2) (Last updated: December 29, 2015). Available from, as of May 25, 2016: https://echa.europa.eu/


5.4 Mechanism of Action

Glycogenic, by L-Proline oxidase in the kidney, it is ring-opened and is oxidized to form L-Glutamic acid. L-Ornithine and L-Glutamic acid are converted to L-Proline via L-Glutamic acid-gamma-semialdehyde. It is contained abundantly in collagen, and is intimately involved in the function of arthrosis and chordae.


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28-May-2025
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ABOUT THIS PAGE

Looking for 147-85-3 / Proline API manufacturers, exporters & distributors?

Proline manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Proline API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Proline manufacturer or Proline supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Proline manufacturer or Proline supplier.

PharmaCompass also assists you with knowing the Proline API Price utilized in the formulation of products. Proline API Price is not always fixed or binding as the Proline Price is obtained through a variety of data sources. The Proline Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Proline

Synonyms

L-proline, 147-85-3, L-(-)-proline, (s)-pyrrolidine-2-carboxylic acid, (2s)-pyrrolidine-2-carboxylic acid, H-pro-oh

Cas Number

147-85-3

Unique Ingredient Identifier (UNII)

9DLQ4CIU6V

About Proline

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 Manufacturers

A Proline manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Proline, including repackagers and relabelers. The FDA regulates Proline manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Proline API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Proline manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Proline Suppliers

A Proline supplier is an individual or a company that provides Proline active pharmaceutical ingredient (API) or Proline finished formulations upon request. The Proline suppliers may include Proline API manufacturers, exporters, distributors and traders.

click here to find a list of Proline suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Proline USDMF

A Proline DMF (Drug Master File) is a document detailing the whole manufacturing process of Proline active pharmaceutical ingredient (API) in detail. Different forms of Proline DMFs exist exist since differing nations have different regulations, such as Proline USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Proline DMF submitted to regulatory agencies in the US is known as a USDMF. Proline USDMF includes data on Proline's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Proline USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Proline suppliers with USDMF on PharmaCompass.

Proline JDMF

The Pharmaceuticals and Medical Devices Agency (PMDA) established the Japan Drug Master File (JDMF), also known as the Master File (MF), to permit Japanese and foreign manufacturers of drug substances, intermediates, excipients, raw materials, and packaging materials (‘Products’) to voluntarily register confidential information about the production and management of their products in Japan.

The Proline Drug Master File in Japan (Proline JDMF) empowers Proline API manufacturers to present comprehensive information (e.g., production methods, data, etc.) to the review authority, i.e., PMDA (Pharmaceuticals & Medical Devices Agency).

PMDA reviews the Proline JDMF during the approval evaluation for pharmaceutical products. At the time of Proline JDMF registration, PMDA checks if the format is accurate, if the necessary items have been included (application), and if data has been attached.

click here to find a list of Proline suppliers with JDMF on PharmaCompass.

Proline CEP

A Proline CEP of the European Pharmacopoeia monograph is often referred to as a Proline Certificate of Suitability (COS). The purpose of a Proline CEP is to show that the European Pharmacopoeia monograph adequately controls the purity of Proline EP produced by a given manufacturer. Suppliers of raw materials can prove the suitability of Proline to their clients by showing that a Proline CEP has been issued for it. The manufacturer submits a Proline CEP (COS) as part of the market authorization procedure, and it takes on the role of a Proline CEP holder for the record. Additionally, the data presented in the Proline CEP (COS) is managed confidentially and offers a centralized system acknowledged by numerous nations, exactly like the Proline DMF.

A Proline CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. Proline CEPs may be accepted in nations that are not members of the Ph. Eur. at the discretion of the authorities there.

click here to find a list of Proline suppliers with CEP (COS) on PharmaCompass.

Proline NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Proline as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Proline API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Proline as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Proline and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Proline NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Proline suppliers with NDC on PharmaCompass.

Proline GMP

Proline Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Proline GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Proline GMP manufacturer or Proline GMP API supplier for your needs.

Proline CoA

A Proline CoA (Certificate of Analysis) is a formal document that attests to Proline's compliance with Proline specifications and serves as a tool for batch-level quality control.

Proline CoA mostly includes findings from lab analyses of a specific batch. For each Proline CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Proline may be tested according to a variety of international standards, such as European Pharmacopoeia (Proline EP), Proline JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Proline USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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