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    Chemistry

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    Also known as: Cyclic somatostatin, 38916-34-6, Somatostatine, Somatostatina, Somatostatinum, Somatostatin-14
    Molecular Formula
    C76H104N18O19S2
    Molecular Weight
    1637.9  g/mol
    InChI Key
    NHXLMOGPVYXJNR-ATOGVRKGSA-N
    Somatostatin
    A 14-amino acid peptide named for its ability to inhibit pituitary GROWTH HORMONE release, also called somatotropin release-inhibiting factor. It is expressed in the central and peripheral nervous systems, the gut, and other organs. SRIF can also inhibit the release of THYROID-STIMULATING HORMONE; PROLACTIN; INSULIN; and GLUCAGON besides acting as a neurotransmitter and neuromodulator. In a number of species including humans, there is an additional form of somatostatin, SRIF-28 with a 14-amino acid extension at the N-terminal.
    1 2D Structure

    Somatostatin

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (4R,7S,10S,13S,16S,19S,22S,25S,28S,31S,34S,37R)-19,34-bis(4-aminobutyl)-31-(2-amino-2-oxoethyl)-37-[[2-[[(2S)-2-aminopropanoyl]amino]acetyl]amino]-13,25,28-tribenzyl-10,16-bis[(1R)-1-hydroxyethyl]-7-(hydroxymethyl)-22-(1H-indol-3-ylmethyl)-6,9,12,15,18,21,24,27,30,33,36-undecaoxo-1,2-dithia-5,8,11,14,17,20,23,26,29,32,35-undecazacyclooctatriacontane-4-carboxylic acid
    2.1.2 InChI
    InChI=1S/C76H104N18O19S2/c1-41(79)64(100)82-37-61(99)83-58-39-114-115-40-59(76(112)113)92-72(108)57(38-95)91-75(111)63(43(3)97)94-71(107)54(33-46-23-11-6-12-24-46)90-74(110)62(42(2)96)93-66(102)51(28-16-18-30-78)84-69(105)55(34-47-36-81-49-26-14-13-25-48(47)49)88-68(104)53(32-45-21-9-5-10-22-45)86-67(103)52(31-44-19-7-4-8-20-44)87-70(106)56(35-60(80)98)89-65(101)50(85-73(58)109)27-15-17-29-77/h4-14,19-26,36,41-43,50-59,62-63,81,95-97H,15-18,27-35,37-40,77-79H2,1-3H3,(H2,80,98)(H,82,100)(H,83,99)(H,84,105)(H,85,109)(H,86,103)(H,87,106)(H,88,104)(H,89,101)(H,90,110)(H,91,111)(H,92,108)(H,93,102)(H,94,107)(H,112,113)/t41-,42+,43+,50-,51-,52-,53-,54-,55-,56-,57-,58-,59-,62-,63-/m0/s1
    2.1.3 InChI Key
    NHXLMOGPVYXJNR-ATOGVRKGSA-N
    2.1.4 Canonical SMILES
    CC(C1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)CCCCN)CC2=CNC3=CC=CC=C32)CC4=CC=CC=C4)CC5=CC=CC=C5)CC(=O)N)CCCCN)NC(=O)CNC(=O)C(C)N)C(=O)O)CO)C(C)O)CC6=CC=CC=C6)O
    2.1.5 Isomeric SMILES
    C[C@H]([C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CCCCN)CC2=CNC3=CC=CC=C32)CC4=CC=CC=C4)CC5=CC=CC=C5)CC(=O)N)CCCCN)NC(=O)CNC(=O)[C@H](C)N)C(=O)O)CO)[C@@H](C)O)CC6=CC=CC=C6)O
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Cyclic Somatostatin

    2. Somatofalk

    3. Somatostatin 14

    4. Somatostatin, Cyclic

    5. Somatostatin-14

    6. Somatotropin Release Inhibiting Factor

    7. Somatotropin Release Inhibiting Hormone

    8. Somatotropin Release-inhibiting Factor

    9. Somatotropin Release-inhibiting Hormone

    10. Srih-14

    11. Stilamin

    2.2.2 Depositor-Supplied Synonyms

    1. Cyclic Somatostatin

    2. 38916-34-6

    3. Somatostatine

    4. Somatostatina

    5. Somatostatinum

    6. Somatostatin-14

    7. Synthetic Somatostatin-14

    8. Somatostatin (sheep)

    9. Somatostatin 14

    10. Synthetic Growth Hormone Release-inhibiting Hormone

    11. Chebi:64628

    12. Somatostatin, Cyclic

    13. Stilamin

    14. Srif 14

    15. 15-28-somatostatin-28

    16. Somatostatine [inn-french]

    17. Somatostatinum [inn-latin]

    18. Somatostatina [inn-spanish]

    19. Somatostatin (rat)

    20. Ccris 3629

    21. Somatostatin (human)

    22. Somatostatin (pigeon)

    23. Einecs 254-186-5

    24. Somatostatin [inn:ban]

    25. Somatostatin-1

    26. Unii-6e20216q0l

    27. Sr 9357

    28. Somatostatin-14srif-14

    29. Chembl1823872

    30. Schembl21361053

    31. Bdbm81767

    32. Growth Hormone Inhibiting Hormone

    33. Akos015994634

    34. 6e20216q0l

    35. Db09099

    36. Hs-2027

    37. Ncgc00167137-01

    38. Growth Hormone-release Inhibiting Factor: L-alanylglycyl-l-cysteinyl-l-lysyl-l-asparaginyl-l-phenylalanyl-l-phenylalanyl-l-tryptophyl-l-lysyl-l-threonyl-l-phenylalanyl-l-threonyl-l-seryl-l-cysteine Cyclic (3-14) Disulfide

    39. Cas_38916-34-6

    40. Cb6417646

    41. C74981

    42. 916s346

    43. Brd-k14681867-015-01-6

    44. Q22075835

    45. Ala-gly-cyclo-[cys-lys-asn-phe-phe-trp-lys-thr-phe-thr-ser-cys]

    46. L-alanyl-n-[(4r,7s,10s,13s,16s,19s,22s,25s,28s,31s,34s,37r)-19,34-bis(4-aminobutyl)-31-(2-amino-2-oxoethyl)-13,25,28-tribenzyl-4-carboxy-10,16-bis[(1r)-1-hydroxyethyl]-7-(hydroxymethyl)-22-(1h-indol-3-ylmethyl)-6,9,12,15,18,21,24,27,30,33,36-undecaoxo-1,2-dithia-5,8,11,14,17,20,23,26,29,32,35-undecaazacyclooctatriacontan-37-yl]glycinamide

    47. L-alanylglycyl-l-cysteinyl-l-lysyl-l-asparaginyl-l-phenylalanyl-l-phenylalanyl-l-tryptophyl-l-lysyl-l-threonyl-l-phenylalanyl-l-threonyl-l-seryl-l-cysteine Cyclic (3-14) Disulfide

    48. Somatostatin-14 (h-l-ala-l-gly-l-cys(1)-l-lys-l-asn-l-phe-l-phe-l-trp-l-lys-l-thr-l-phe-l-thr-l-ser-l-cys(1)-oh)

    2.3 Create Date
    2007-07-03
    3 Chemical and Physical Properties
    Molecular Weight 1637.9 g/mol
    Molecular Formula C76H104N18O19S2
    XLogP3-3.1
    Hydrogen Bond Donor Count22
    Hydrogen Bond Acceptor Count24
    Rotatable Bond Count26
    Exact Mass1636.71665551 g/mol
    Monoisotopic Mass1636.71665551 g/mol
    Topological Polar Surface Area664 Ų
    Heavy Atom Count115
    Formal Charge0
    Complexity3240
    Isotope Atom Count0
    Defined Atom Stereocenter Count15
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For the symptomatic treatment of acute bleeding from esophageal varices. Other treatment options for long-term management of the condition may be considered if necessary, once initial control has been established.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Somatostatin is an endogenous peptide hormone that is secreted by the central nervous system, gastrointestinal tract, retina, peripheral neurons and pancreatic D cells of the islets of Langerhans. It exhibits several biological roles but predominantly exerts an inhibitory effect on secretion of other hormones and transmitters. While distribution of two active isoforms of somatostatin is similar, SST-14 is more predominant in the enteric neurons and peripheral nerves whereas SST-28 is more prominent in the retina and intestinal mucosal cells. **Anterior pituitary gland and brain:** It inhibits the release of growth hormones and thyroid-stimulating hormones, such as thyroid stimulating hormone (TSH) and thyrotrophin, from the anterior pituitary while inhibiting the release of dopamine from the midbrain, norepinephrine, TRH and corticotrophin-releasing hormone in the brain. **Pancreas:** In the pancreas, somatostatin reduces the secretion of glucagon and insulin as well as bicarbonate ions and other enzymes. **Thyroid gland:** Somatosatin reduces secretion of T3, T4, and calcitonin. Somatostatin regulates the thyroid function by reducing basal TSH release. **Gastrointestinal tract:** It attenuates the release of most gastrointestinal hormones such as gastrin, secretin, motilin, gastric acid, enteroglucagon, cholecystokinin (CCK), vasoactive intestinal peptide (VIP), gastric inhibitory polypeptide (GIP), intrinsic factor, pepsin, neurotensin, as well as bile secretion and colonic fluid secretion. **Adrenal gland:** It inhibits angiotensin II-stimulated aldosterone secretion and acetylcholine-induced medullary catecholamine secretion. **Eye/retina:** Somatostatin inhibits the production of vascular endothelial growth factor. **Inflammatory cells and sensory nerves:** The expression of somatostatin has been found in inflammatory cells such as lymphocytes, monocytes, macrophages and endothelial cells to act as an autocrine or paracrine regulator in local immune responses. Findings suggest that somatostatin may play a role in exerting local and systemic anti-inflammatory and antinociceptive effects. On primary afferent neurons, somatostatin reduces the responses to thermal stimulation in C-mechanoheat sensitive fibers in a dose-dependent fashion and reduces the responses of C-mechanoheat fibers to bradykinin-induced excitation and sensitization to heat. Somatostatin is reported to elicit an analgesic effect when applied intrathecally; there is evidence supporting that similar effects may occur when systemically used to treat endocrine disorders. Somatostatin is thought to reduce bleeding from esophageal varices by causing splanchnic vasoconstriction. Somatostatin elicits anti-neoplastic actions on various tumours via direct or indirect effects, or a combination of both.

    5.2 MeSH Pharmacological Classification

    Hormones

    Chemical substances having a specific regulatory effect on the activity of a certain organ or organs. The term was originally applied to substances secreted by various ENDOCRINE GLANDS and transported in the bloodstream to the target organs. It is sometimes extended to include those substances that are not produced by the endocrine glands but that have similar effects. (See all compounds classified as Hormones.)

    5.3 ATC Code

    H - Systemic hormonal preparations, excl. sex hormones and insulins

    H01 - Pituitary and hypothalamic hormones and analogues

    H01C - Hypothalamic hormones

    H01CB - Somatostatin and analogues

    H01CB01 - Somatostatin

    5.4 Absorption, Distribution and Excretion

    Absorption

    This pharmacokinetic data is irrelevant.

    Route of Elimination

    As a polypeptide chain, somatostatin is primarily eliminated via metabolism by peptidase enzymes.

    Volume of Distribution

    This pharmacokinetic data is irrelevant.

    Clearance

    Following intravenous administration of 3H-labeld endogenous somatostatin, the total body clearance was approximately 50 mL/min. In man, the value was calculated to be as high as 3000 mL/minutes, which is greatly exceeds the hepatic blood flow. This suggests that rapid enzymatic breakdown in the circulation and other tissues serves as a critical route of elimination.

    5.5 Metabolism/Metabolites

    Somatostatin is rapidly degraded by peptidase enzymes present in cells and plasma.

    5.6 Biological Half-Life

    The half-life of endogenous somatostatin is 1-3 minutes due to rapid degradation by peptidase enzymes present in the plasma and tissues.

    5.7 Mechanism of Action

    Somatostatin binds to 5 subtypes of somatostatin receptors (SSTRs), which are all Gi-protein-coupled transmembrane receptors that inhibits adenylyl cyclase upon activation. By inhibiting intracellular cyclic AMP and Ca2+ and by a receptor-linked distal effect on exocytosis, SSTRs block cell secretion. The common pathway shared by the receptors involve the activation of phosphotyrosine phosphatase (PTP), and modulation of mitogen-activated protein kinase (MAPK). With the exception of SSTR3, activation of SSTRs lead to activation of voltage-gated potassium channels accompanied by increased K+ currents. This result in membrane hyperpolarization and inhibits depolarization-induced Ca2+ influx through voltage-sensitive Ca2+ channels. Depending on the receptor subtype, signalling cascades involve activation of other downstream targets such as Na+/H+ exchanger, Rho GTPase, and nitric oxide synthase (NOS). SSTRs 1 to 4 bind both somatostatin isoforms with equal nanomolar binding affinity whereas SSTR5 exhibits a 5- to 10-fold higher binding affinity for SST-28. **Effects of SSTR1:** Upon biding of somatostatin and activation, SSTR1 mediates an antisecretory effect on growth hormone, prolactin and calcitonin. **Effects of SSTR2:** SSTR2 subtype dominates in endocrine tissues. By binding to SST2 receptors, somatostatin exerts paracrine inhibitory actions on gastrin release from G cells, histamine release from ECL cells, and directly on parietal cell acid output. SSTR2 receptor signalling cascades also inhibit the secretion of growth hormone and that of adrenocorticotropin, glucagon, insulin, and interferon-. **Effects of SSTR3:** Activation of these receptors lead to reduction in cell proliferation. SSTR3 triggers PTP-dependent cell apoptosis accompanied by activation of p53 and the pro-apoptotic protein Bax. A study of the matrigel sponge assay suggests that through SSTR3-mediated inhibition of both NOS and MAPK activities may lead to the antitumor effects of somatostatin in inhibiting tumor angiogenesis. **Effects of SSTR4:** The functions of SSTR4 remain largely unknown. **Effects of SSTR5:** Like SSTR2, SSTR5 subtype also predominates in endocrine tissues. Upon activation, SSTR5 signalling cascades exert an inhibitory action on growth hormone, adrenocorticotropin, insulin, and glucagon-like peptide-1 as well as the secretion of amylase. The presence of somatostatin receptors has been identified in most neuroendocrine tumours, endocrine gastroenteropancreatic (GEP) tumors, paragangliomas, pheochromocytomas, medullary thyroid carcinomas (MTC) and small cell lung carcinomas. The antitumor effects of somatostatin were also effective in various malignant lymphomas and breast tumours. Gastrointestinal hormones, such as gastrin, secretin, and cholecystokinin (CCK), as well as growth hormones and growth factors are thought to be elevated in gastrointestinal tract and neuroendocrine tumours and are inhibited by somatostatin. _In vitro_, somatostatin inhibited epidermal growth factor (EGF)-induced DNA synthesis and replication following which suggest that somatostatin may have direct anti-proliferative effects via SSTR signalling. Acromegaly is characterized as the endocrine disorder caused by a functioning tumour of cells that secrete growth hormone from the anterior pituitary. Somatostatin analogue therapies serve to normalize the elevated levels of GH and insulin-like growth factor 1 (IGF-1) and attenuate tumour growth. In the vascular system this likely produces vasoconstriction by inhibiting adenylate cyclase leading to a lowering the concentration of cyclic adenosine monophosphate in the endothelial cells which ultimately blocks vasodilation through this pathway. This vasoconstriction is though the be responsible for reducing blood flow to the esophageal tissues and so reduces bleeding from esophageal varices. Somatostatin mediates an analgesic activity by reducing vascular and nociceptive components of inflammation. Studies indicate that somatostatin may be present in nociceptive DRG neurons with C-fibers and primary afferent neurons to inhibit the release of transmitters at the presynaptic junctions of the sensory-efferent nerve terminals. Exogenous somatostatin has shown to inhibit the release of Substance P from central and peripheral nerve ending.

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    07-May-2021
    29-Jan-2024
    KGS
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    ABOUT THIS PAGE

    Somatostatin Manufacturers

    A Somatostatin manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Somatostatin, including repackagers and relabelers. The FDA regulates Somatostatin manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Somatostatin 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 Somatostatin manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

    Somatostatin Suppliers

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

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

    Somatostatin USDMF

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

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

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

    Somatostatin KDMF

    In Korea, the Ministry of Food and Drug Safety (MFDS) is in charge of regulating pharmaceutical products and services.

    Pharmaceutical companies submit a Somatostatin Drug Master File in Korea (Somatostatin KDMF) to the MFDS, which includes comprehensive information about the production, processing, facilities, materials, packaging, and testing of Somatostatin. The MFDS reviews the Somatostatin KDMF as part of the drug registration process and uses the information provided in the Somatostatin KDMF to evaluate the safety and efficacy of the drug.

    After submitting a Somatostatin KDMF to the MFDS, the registered manufacturer can provide importers or distributors with the registration number without revealing confidential information to Korean business partners. Applicants seeking to register their Somatostatin API can apply through the Korea Drug Master File (KDMF).

    click here to find a list of Somatostatin suppliers with KDMF on PharmaCompass.

    Somatostatin CEP

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

    A Somatostatin CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. Somatostatin 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 Somatostatin suppliers with CEP (COS) on PharmaCompass.

    Somatostatin WC

    A Somatostatin written confirmation (Somatostatin WC) is an official document issued by a regulatory agency to a Somatostatin manufacturer, verifying that the manufacturing facility of a Somatostatin active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Somatostatin APIs or Somatostatin finished pharmaceutical products to another nation, regulatory agencies frequently require a Somatostatin WC (written confirmation) as part of the regulatory process.

    click here to find a list of Somatostatin suppliers with Written Confirmation (WC) on PharmaCompass.

    Somatostatin GMP

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

    Somatostatin CoA

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

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

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