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Chemistry

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Also known as: 7-angelyleuropine, (-)-lasiocarpine, 303-34-4, Europine 7-angelate, Nsc-30625, Nci-c01478
Molecular Formula
C21H33NO7
Molecular Weight
411.5  g/mol
InChI Key
QHOZSLCIKHUPSU-LPLKQDONSA-N
FDA UNII
S770100Q96

Lasiocarpine
(1S,7aR)-7-({[(2R)-2,3-dihydroxy-2-[(1S)-1-methoxyethyl]-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (2Z)-2-methylbut-2-enoate is a natural product found in Heliotropium arbainense, Heliotropium suaveolens, and other organisms with data available.
1 2D Structure

Lasiocarpine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(7S,8R)-7-[(Z)-2-methylbut-2-enoyl]oxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2R)-2,3-dihydroxy-2-[(1S)-1-methoxyethyl]-3-methylbutanoate
2.1.2 InChI
InChI=1S/C21H33NO7/c1-7-13(2)18(23)29-16-9-11-22-10-8-15(17(16)22)12-28-19(24)21(26,14(3)27-6)20(4,5)25/h7-8,14,16-17,25-26H,9-12H2,1-6H3/b13-7-/t14-,16-,17+,21-/m0/s1
2.1.3 InChI Key
QHOZSLCIKHUPSU-LPLKQDONSA-N
2.1.4 Canonical SMILES
CC=C(C)C(=O)OC1CCN2C1C(=CC2)COC(=O)C(C(C)OC)(C(C)(C)O)O
2.1.5 Isomeric SMILES
C/C=C(/C)\C(=O)O[C@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@@]([C@H](C)OC)(C(C)(C)O)O
2.2 Other Identifiers
2.2.1 UNII
S770100Q96
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Lasiocarpine Hydrochloride, (1s-(1alpha(z),7(2s*,3r*),7aalpha))-isomer

2. Lasiocarpine Sulfate, (1s-(1alpha(z),7(2s*,3r*),7aalpha))-isomer

2.3.2 Depositor-Supplied Synonyms

1. 7-angelyleuropine

2. (-)-lasiocarpine

3. 303-34-4

4. Europine 7-angelate

5. Nsc-30625

6. Nci-c01478

7. S770100q96

8. Rcra Waste Number U143

9. Mls002639334

10. Heliotridine Ester With Lasiocarpum And Angelic Acid

11. Ccris 355

12. Nsc30625

13. C21h33no7

14. Hsdb 6062

15. Unii-s770100q96

16. Nsc 30625

17. Heliotridine Ester With Lasiocarpum & Angelic Acid

18. Ai3-51770

19. Lasiocarpine [mi]

20. Lasiocarpine, Hplc Grade

21. Rcra Waste No. U143

22. Lasiocarpine [hsdb]

23. Lasiocarpine [iarc]

24. Schembl168932

25. Chembl1999554

26. Mfcd31631257

27. Zinc61997632

28. Heliosupine Methyl Ether [mi]

29. Akos030501885

30. (z)-2-methylcrotonic Acid, 2,3-dihydroxy-2-(1-methoxyethyl)-3-methylbutyrate (ester)

31. (7alpha-angelyloxy-5,6,7,8alpha-tetrahydro-3h-pyrrolizin-1-yl)methyl-2,3-dihydroxy-2-(1'-methoxyethyl)-3-methylbutyrate

32. 2,3,5,7alphabeta-tetrahydro-1-hydroxy-1h-pyrrolizine-7-methanol-1-angelate-7-(2,3-dihydroxy-2(1-methoxyethyl))-3-methyl-butyrate

33. 2-butenoic Acid, 2-methyl-, 7-((2,3-dihydroxy-2-(1-methoxyethyl)-3-methyl-1-oxobutoxy)methyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-yl Ester, (1s-(1alpha(z),7(2s*,3r*),7aalpha))-

34. Wln: T55 An Cutj D1ovxqxq1 & 1 & Y1 & O1 Fovy1 & U2

35. (1s,7ar)-7-((((r)-2,3-dihydroxy-2-((s)-1-methoxyethyl)-3-methylbutanoyl)oxy)methyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-yl (z)-2-methylbut-2-enoate

36. 2-butenoic Acid, 2-methy-,(1s,7ar)-7-(((2r)-2,3-dihydroxy-2-((1s)-1-methoxyethyl)-3-methyl-1-oxobutoxy)methyl)-2,3,5,7a-tetrahydro-1h-ester, (2z)-

37. 2-butenoic Acid, 2-methyl-, 7-((2,3-dihydroxy-2-(1-methoxyethyl)-3-methyl-1-oxobutoxy)methyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-yl Ester, (1s-(1.alpha.(z),7(s*(r*)),7a.alpha.))-

38. 2-butenoic Acid, 2-methyl-, 7-((2,3-dihydroxy-2-(1-methoxyethyl)-3-methyl-1-oxobutoxy)methyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-yl Ester, (1s-(1alpha(z),7(2s*,3r*),7a Alpha))-

39. 2-butenoic Acid, 7-[[2,3-dihydroxy-2-(1-methoxyethyl)-3-methyl-1-oxobutoxy]methyl]-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-yl Ester, [1s-[1.alpha.(z),7(2s*,3r*),7a.alpha.]]-

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 411.5 g/mol
Molecular Formula C21H33NO7
XLogP30.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count8
Rotatable Bond Count10
Exact Mass411.22570239 g/mol
Monoisotopic Mass411.22570239 g/mol
Topological Polar Surface Area106 Ų
Heavy Atom Count29
Formal Charge0
Complexity699
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Absorption, Distribution and Excretion

LASROCARPINE (RANDOMLY LABELLED, 44% IN THE AMINO ALCOHOL) WAS ADMIN IP TO RATS (TOTAL DOSE, 5 MG) DISTRIBUTION OF LABEL AFTER 4 HR WAS AS FOLLOWS: CARCASS, 6.4%; INTESTINES, 8.6%; TESTES, 0.1%; LUNG, 0.05%; KIDNEY, 0.26%; HEART, 0.05%; SPLEEN, 0.01%; BRAIN, 0.03%; URINE, 27.2%; LIVER, 2.8%, EXPIRED CO2, 9.3% FRACTIONATION OF LIVER RESULTED IN 1.73% IN A TRICHLOROACETIC ACID EXTRACT, 0.6% IN PROTEIN, 0.48% IN LIPID & 0.005% IN NUCLEIC ACIDS.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V10 285 (1976)


4.2 Metabolism/Metabolites

STUDIES WITH LASIOCARPINE HAVE CONFIRMED THE FORMATION OF PYRROLIC METABOLITES BY THE MIXED-FUNCTION OXIDASE SYSTEM OF THE MICROSOMAL FRACTION OF RAT LIVER. DEHYDROHELIOTRIDINE HAS BEEN ISOLATED & IDENTIFIED AS A PRODUCT OF MICROSOMAL OXIDATION OF LASIOCARPINE.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V10 285 (1976)


IN URINE ... OBTAINED 16 HR AFTER INJECTION ... TO RATS ... UNCHANGED LASIOCARPINE (1-1.5% OF DOSE), HELIOTRIDINE (1.5-3%), HELIOTRIDINE N-OXIDE (6%) & TRACES OF BASES WITH CHROMATOGRAPHIC PROPERTIES OF EUROPINE & 7-ANGELYHELIOTRIDINE (EXPECTED PRODUCTS OF PARTIAL HYDROLYSIS). ... METABOLITES IN 24-HR URINE SAMPLE ... 8.5% OF ADMIN LASIOCARPINE.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V10 286 (1976)


HUMAN EMBRYONIC LIVER SLICES CONVERTED THE PYRROLIZIDINE ALKALOID LASIOCARPINE INTO PYRROLES, AS INDICATED BY A POS EHRLICH COLOR REACTION, WHEREAS LUNG TISSUE DID NOT.

ARMSTRONG SJ, ZUCKERMAN AJ; NATURE (LONDON) 228 (5271): 569 (1970)


4.3 Mechanism of Action

Death may be due to actual liver damage or to the upsetting of the copper storage mechanism which leads to a build-up of copper in the organ, resulting in the acute hemolytic crisis associated with chronic copper poisoning.

Humphreys, D.J. Veterinary Toxicology. 3rd ed. London, England: Bailliere Tindell, 1988., p. 236


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Lasiocarpine manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Lasiocarpine 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 Lasiocarpine manufacturer or Lasiocarpine supplier for your needs.

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

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

API | Excipient name

Lasiocarpine

Synonyms

7-angelyleuropine, (-)-lasiocarpine, 303-34-4, Europine 7-angelate, Nsc-30625, Nci-c01478

Cas Number

303-34-4

Unique Ingredient Identifier (UNII)

S770100Q96

About Lasiocarpine

(1S,7aR)-7-({[(2R)-2,3-dihydroxy-2-[(1S)-1-methoxyethyl]-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (2Z)-2-methylbut-2-enoate is a natural product found in Heliotropium arbainense, Heliotropium suaveolens, and other organisms with data available.

Lasiocarpine Manufacturers

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

Lasiocarpine Suppliers

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

Lasiocarpine GMP

Lasiocarpine 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 Lasiocarpine 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 Lasiocarpine GMP manufacturer or Lasiocarpine GMP API supplier for your needs.

Lasiocarpine CoA

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

Lasiocarpine CoA mostly includes findings from lab analyses of a specific batch. For each Lasiocarpine 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.

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