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Chemistry

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Also known as: L-histidine, 71-00-1, H-his-oh, Glyoxaline-5-alanine, L-(-)-histidine, Anti-rheuma

Molecular Formula

C₆H₉N₃O₂

Molecular Weight

155.15 g/mol

InChI Key

HNDVDQJCIGZPNO-YFKPBYRVSA-N

FDA UNII

4QD397987E

An essential amino acid that is required for the production of HISTAMINE.

1 2D Structure

L-Histidine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid

2.1.2 InChI

InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m0/s1

2.1.3 InChI Key

HNDVDQJCIGZPNO-YFKPBYRVSA-N

2.1.4 Canonical SMILES

C1=C(NC=N1)CC(C(=O)O)N

2.1.5 Isomeric SMILES

C1=C(NC=N1)C[C@@H](C(=O)O)N

2.2 Other Identifiers

2.2.1 UNII

4QD397987E

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Histidine, L Isomer

2. Histidine, L-isomer

3. L-histidine

4. L-isomer Histidine

2.3.2 Depositor-Supplied Synonyms

1. L-histidine

2. 71-00-1

3. H-his-oh

4. Glyoxaline-5-alanine

5. L-(-)-histidine

6. Anti-rheuma

7. Istidina

8. S-histidine

9. (l)-histidine

10. Histidine (van)

11. Histidine, L-

12. Histidina

13. (s)-4-(2-amino-2-carboxyethyl)imidazole

14. (2s)-2-amino-3-(1h-imidazol-4-yl)propanoic Acid

15. L-histidin

16. (s)-alpha-amino-1h-imidazole-4-propanoic Acid

17. Fema No. 3694

18. Histidine [usan:inn]

19. Histidinum [inn-latin]

20. (s)-histidine

21. Histidina [inn-spanish]

22. L-beta-(4-imidazolyl)alanin

23. 4-(2-amino-2-carboxyethyl)imidazole

24. His

25. L-hystidine

26. 1h-imidazole-4-alanine, (s)-

27. L-hisidine

28. (s)-2-amino-3-(4-imidazolyl)propionsaeure

29. L-beta-(4-imidazolyl)-alpha-alanin

30. (s)-alpha-amino-1h-imidazole-4-propionic Acid

31. L-his

32. L-alanine, 3-(1h-imidazol-4-yl)-

33. Ai3-26558

34. Alpha-amino-4(or 5)-imidazolepropionic Acid

35. Histidine (l-histidine)

36. Alpha-amino-1h-imidazole-4-propionic Acid, (s)-

37. 1h-imidazole-4-propanoic Acid, Alpha-amino-, (s)-

38. (s)-a-amino-1h-imidazole-4-propanoic Acid

39. (s)-2-amino-3-(4-imidazolyl)propionic Acid

40. Chebi:15971

41. 4qd397987e

42. Nsc-137773

43. 7006-35-1

44. Histidinum

45. Mfcd00064315

46. (2s)-2-amino-3-(imidazol-4-yl)propanoic Acid

47. Histidine, Monohydrochloride

48. Hsdb 1810

49. Einecs 200-745-3

50. Nsc 137773

51. Unii-4qd397987e

52. 1hsl

53. 1lag

54. [3h]histidine

55. Histidine,(s)

56. [3h]-histidine

57. (2s)-2-amino-3-(1h-imidazol-4-yl)propanoic Acid Hydrochloride

58. Histidine (usp/inn)

59. Histidine [inn]

60. Histidine [ii]

61. Histidine [mi]

62. L-histidine (jp17)

63. L-2-amino-3-(4-imidazolyl)propionic Acid

64. Histidine [hsdb]

65. Histidine [inci]

66. Histidine [usan]

67. Histidine [vandf]

68. Lopac-h-8125

69. Bmse000039

70. Bmse000976

71. Bmse001015

72. Histidine [mart.]

73. L-histidine [fcc]

74. L-histidine [jan]

75. L-histidine (h-his-oh)

76. Amino-4-imidazoleproprionate

77. Histidine [who-dd]

78. L-histidine [fhfi]

79. Schembl3259

80. Lopac0_000566

81. Us9138393, Histidine

82. Us9144538, Histidine

83. (s)1h-imidazole-4-alanine

84. Chembl17962

85. L-histidine [usp-rs]

86. (2s)-2-amino-3-(1h-imidazol-5-yl)propanoic Acid

87. (s)-1h-imidazole-4-alanine

88. Bdbm7953

89. Gtpl3310

90. Gtpl4670

91. L-histidine, Non-animal Source

92. Imidazole C-4(5) Deriv. 5

93. Amino-4-imidazoleproprionic Acid

94. Dtxsid9023126

95. Histidine [ep Monograph]

96. Amino-1h-imidazole-4-propanoate

97. Histidine [usp Monograph]

98. L-histidine, P.a., 98.5%

99. Bdbm181118

100. L-histidine, Cell Culture Reagent

101. 3-(1h-imidazol-4-yl)-l-alanine

102. Hy-n0832

103. Zinc6661227

104. Amino-1h-imidazole-4-propanoic Acid

105. Akos015854051

106. Akos026676613

107. Am81801

108. Ccg-204656

109. Cs-7781

110. Db00117

111. Sdccgsbi-0050549.p002

112. Serine Impurity C [ep Impurity]

113. (s)-a-amino-1h-imidazole-4-propanoate

114. Ncgc00015518-01

115. Ncgc00162189-01

116. Ncgc00162189-02

117. Ncgc00162189-05

118. Ac-35086

119. As-14171

120. (s)-alpha-amino-1h-imidazole-4-propanoate

121. (s)-alpha-amino-1h-imidazole-4-propionate

122. L-histidine, Bioultra, >=99.5% (nt)

123. H0149

124. L-histidine, Saj Special Grade, >=98.5%

125. S3989

126. C00135

127. D00032

128. D70843

129. H-2310

130. L-histidine, Reagentplus(r), >=99% (tlc)

131. M02982

132. L-histidine, Vetec(tm) Reagent Grade, >=99%

133. (s)-2-amino-3-(1h-imidazol-4-yl)propanoic Acid

134. 064h315

135. Q485277

136. B81aedb0-eaca-4296-9bab-52d60f137ffb

137. 1h-imidazole-4-propanoic Acid, .alpha.-amino-, (s)-

138. F8881-8926

139. F8889-0575

140. L-histidine, Certified Reference Material, Tracecert(r)

141. Z955123622

142. Histidine, European Pharmacopoeia (ep) Reference Standard

143. L-histidine, United States Pharmacopeia (usp) Reference Standard

144. L-histidine, Pharmaceutical Secondary Standard; Certified Reference Material

145. L-histidine, Cell Culture Tested, Meets Ep, Usp Testing Specifications, From Non-animal Source

146. L-histidine, Pharmagrade, Ajinomoto, Ep, 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 Formula	C₆H₉N₃O₂
Molecular Weight	155.15 g/mol
XLogP3	-3.2
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Exact Mass	155.069476538 g/mol
Monoisotopic Mass	155.069476538 g/mol
Topological Polar Surface Area	92 Å²
Heavy Atom Count	11
Formal Charge	0
Complexity	151
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

The actions of supplemental L-histidine are entirely unclear. It may have some immunomodulatory as well as antioxidant activity. L-histidine may be indicated for use in some with rheumatoid arthritis. It is not indicated for treatment of anemia or uremia or for lowering serum cholesterol.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Is found abundantly in hemoglobin; has been used in the treatment of rheumatoid arthritis, allergic diseases, ulcers and anemia. A deficiency can cause poor hearing.

5.2 Absorption, Distribution and Excretion

Absorption

Absorbed from the small intestine via an active transport mechanism requiring the presence of sodium.

ESSENTIAL AMINO ACIDS ARE TRANSFERRED TO FETUS AGAINST A CONCN GRADIENT &, IN THE CASE OF HISTIDINE, NATURAL L-ISOMER HAS BEEN SHOWN TO CROSS SEVERAL TIMES AS FAST AS THE D-ISOMER.

LaDu, B.N., H.G. Mandel, and E.L. Way. Fundamentals of Drug Metabolism and Disposition. Baltimore: Williams and Wilkins, 1971., p. 89

5.3 Metabolism/Metabolites

PRODUCT OF OXIDATIVE DEAMINATION OR TRANSAMINATION OF L-HISTIDINE IS BETA-IMIDAZOLEPYRUVIC ACID; & PRODUCT OF DECARBOXYLATION IS HISTAMINE. HISTAMINE ENTERS OTHER PATHWAYS TO YIELD FURTHER METABOLIC PRODUCTS. /FROM TABLE/

Fenaroli's Handbook of Flavor Ingredients. Volume 2. Edited, translated, and revised by T.E. Furia and N. Bellanca. 2nd ed. Cleveland: The Chemical Rubber Co., 1975., p. 830

5.4 Mechanism of Action

Since the actions of supplemental L-histidine are unclear, any postulated mechanism is entirely speculative. However, some facts are known about L-histidine and some of its metabolites, such as histamine and trans-urocanic acid, which suggest that supplemental L-histidine may one day be shown to have immunomodulatory and/or antioxidant activities. Low free histidine has been found in the serum of some rheumatoid arthritis patients. Serum concentrations of other amino acids have been found to be normal in these patients. L-histidine is an excellent chelating agent for such metals as copper, iron and zinc. Copper and iron participate in a reaction (Fenton reaction) that generates potent reactive oxygen species that could be destructive to tissues, including joints.
L-histidine is the obligate precursor of histamine, which is produced via the decarboxylation of the amino acid. In experimental animals, tissue histamine levels increase as the amount of dietary L-histidine increases. It is likely that this would be the case in humans as well. Histamine is known to possess immunomodulatory and antioxidant activity. Suppressor T cells have H2 receptors, and histamine activates them. Promotion of suppressor T cell activity could be beneficial in rheumatoid arthritis. Further, histamine has been shown to down-regulate the production of reactive oxygen species in phagocytic cells, such as monocytes, by binding to the H2 receptors on these cells. Decreased reactive oxygen species production by phagocytes could play antioxidant, anti-inflammatory and immunomodulatory roles in such diseases as rheumatoid arthritis.
This latter mechanism is the rationale for the use of histamine itself in several clinical trials studying histamine for the treatment of certain types of cancer and viral diseases. In these trials, down-regulation by histamine of reactive oxygen species formation appears to inhibit the suppression of natural killer (NK) cells and cytotoxic T lymphocytes, allowing these cells to be more effective in attacking cancer cells and virally infected cells.

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Pfanstiehl

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AMINO GmbH

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Transform your biologic formulations with Pfanstiehl, the industry leader in High-Purity Low Endotoxin Low Metals Parenteral grade excipient manufacturing. Our expertise spans isolation, purification, custom synthesis, and scale-up development, ensuring the highest quality injectable formulation ingredients. Whether you need gram-scale quantities or multi-ton batches, trust Pfanstiehl for the highest quality injectable grade excipients available. The leading pharmaceutical companies worldwide use Pfanstiehl excipients for their unmatched purity, lowest endotoxin, and minimal trace metals. Partner with us to elevate your biologics formulations

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, RING ROAD,","city":"BANGALORE, KARNATAKA","supplier":"MERCK LIFE SCIENCE KGAA","supplierCountry":"GERMANY","foreign_port":"FRANKFURT\/MAIN INT\\'L","customer":"MERCK GROUP","customerCountry":"INDIA","quantity":"20.00","actualQuantity":"20","unit":"KGS","unitRateFc":"41607","totalValueFC":"9928","currency":"INR","unitRateINR":"41711","date":"28-Oct-2024","totalValueINR":"834219.79","totalValueInUsd":"9928","indian_port":"Bombay Air","hs_no":"29332990","bill_no":"6374572","productDescription":"API","marketType":"REGULATED MARKET","country":"GERMANY","selfForZScoreResived":"Pharma Grade","supplierPort":"FRANKFURT\/MAIN INT\\'L","supplierAddress":"Frankfurter Strasse 25064293 Darmst adt Germany (BENEFICIARY MERCKFINA NCIAL SERVICES GMBH) GERMANY","customerAddress":"50A , RING ROAD,"}]

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country	Total Quantity (KGS)	Average Price (USD/KGS)	Number of Transactions

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INTERMEDIATES SUPPLIERS

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Canada

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South Africa

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CHEMISTRY

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ACTIVE PHARMA INGREDIENTS

16 API Suppliers

6 USDMF

8 CEP/COS

3 JDMF

9 NDC API

5 Listed Suppliers

$ API Reference Price

INTERMEDIATES

1 Intermediates Suppliers

FINISHED DOSAGE FORMULATIONS

52 FDF Dossiers

25 Canada

27 South Africa

RELATED EXCIPIENT COMPANIES

2 Kewpie Corporation

1 Nanjing Well Pharmaceutical

3 Actylis

1 Kerry

1 Pluviaendo

EXCIPIENTS BY APPLICATIONS

5 Parenteral

3 Emulsifying Agents

1 Controlled & Modified Release

1 Film Formers & Plasticizers

1 Coating Systems & Additives

1 Solubilizers

1 Topical

DIGITAL CONTENT

1 DATA COMPILATION #PharmaFlow

3 NEWS #PharmaBuzz

MARKET PLACE

14 APIs

REF. STANDARDS & IMPURITIES

2 EDQM

1 USP

1 Others

ACTIVE PHARMA INGREDIENTS

API REF. PRICE (USD/KG)

$ 72

MARKET PLACE

FINISHED DOSAGE FORMULATIONS

0 DRUGS IN DEVELOPMENT

DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

PATENTS & EXCLUSIVITIES

DIGITAL CONTENT

GLOBAL SALES INFORMATION

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