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    Chemistry

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    Also known as: Glucagonum, Glucagone, His-ser-glu(nh2)-gly-thr-phe-thr-ser-asp-tyr-ser-lys-tyr-leu-asp-ser-arg-arg-ala-glu(nh2)-asp-phe-val-glu(nh2)-trp-leu-met-asp(nh2)-thr, Glucagon-like-immunoreactivity, Glucaton, Bovine glucagon
    Molecular Formula
    C153H225N43O49S
    Molecular Weight
    3482.7  g/mol
    InChI Key
    MASNOZXLGMXCHN-ZLPAWPGGSA-N
    Glucagon
    Recombinant Glucagon is the recombinant form of the endogenous polypeptide hormone Glucagon consisting of 29 amino acids responsible for the release of stored glucose, causing increased blood glucose levels. Clinical Use: Diagnostic Aid for Imaging Studies and Hypoglycemia.
    1 2D Structure

    Glucagon

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (3S)-3-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S,3R)-2-[[2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-amino-3-(1H-imidazol-5-yl)propanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]acetyl]amino]-3-hydroxybutanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-hydroxypropanoyl]amino]hexanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-methylpentanoyl]amino]-3-carboxypropanoyl]amino]-3-hydroxypropanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-carbamimidamidopentanoyl]amino]propanoyl]amino]-5-oxopentanoyl]amino]-4-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-4-amino-1-[[(1S,2R)-1-carboxy-2-hydroxypropyl]amino]-1,4-dioxobutan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic acid
    2.1.2 InChI
    InChI=1S/C153H225N43O49S/c1-72(2)52-97(133(226)176-96(47-51-246-11)132(225)184-104(60-115(159)209)143(236)196-123(78(10)203)151(244)245)179-137(230)103(58-83-64-167-89-29-19-18-28-87(83)89)183-131(224)95(43-46-114(158)208)177-148(241)120(74(5)6)194-141(234)101(54-79-24-14-12-15-25-79)182-138(231)105(61-117(211)212)185-130(223)94(42-45-113(157)207)171-124(217)75(7)170-127(220)91(31-22-49-165-152(160)161)172-128(221)92(32-23-50-166-153(162)163)174-146(239)110(69-199)191-140(233)107(63-119(215)216)186-134(227)98(53-73(3)4)178-135(228)99(56-81-33-37-85(204)38-34-81)180-129(222)90(30-20-21-48-154)173-145(238)109(68-198)190-136(229)100(57-82-35-39-86(205)40-36-82)181-139(232)106(62-118(213)214)187-147(240)111(70-200)192-150(243)122(77(9)202)195-142(235)102(55-80-26-16-13-17-27-80)188-149(242)121(76(8)201)193-116(210)66-168-126(219)93(41-44-112(156)206)175-144(237)108(67-197)189-125(218)88(155)59-84-65-164-71-169-84/h12-19,24-29,33-40,64-65,71-78,88,90-111,120-123,167,197-205H,20-23,30-32,41-63,66-70,154-155H2,1-11H3,(H2,156,206)(H2,157,207)(H2,158,208)(H2,159,209)(H,164,169)(H,168,219)(H,170,220)(H,171,217)(H,172,221)(H,173,238)(H,174,239)(H,175,237)(H,176,226)(H,177,241)(H,178,228)(H,179,230)(H,180,222)(H,181,232)(H,182,231)(H,183,224)(H,184,225)(H,185,223)(H,186,227)(H,187,240)(H,188,242)(H,189,218)(H,190,229)(H,191,233)(H,192,243)(H,193,210)(H,194,234)(H,195,235)(H,196,236)(H,211,212)(H,213,214)(H,215,216)(H,244,245)(H4,160,161,165)(H4,162,163,166)/t75-,76+,77+,78+,88-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,120-,121-,122-,123-/m0/s1
    2.1.3 InChI Key
    MASNOZXLGMXCHN-ZLPAWPGGSA-N
    2.1.4 Canonical SMILES
    CC(C)CC(C(=O)NC(CCSC)C(=O)NC(CC(=O)N)C(=O)NC(C(C)O)C(=O)O)NC(=O)C(CC1=CNC2=CC=CC=C21)NC(=O)C(CCC(=O)N)NC(=O)C(C(C)C)NC(=O)C(CC3=CC=CC=C3)NC(=O)C(CC(=O)O)NC(=O)C(CCC(=O)N)NC(=O)C(C)NC(=O)C(CCCNC(=N)N)NC(=O)C(CCCNC(=N)N)NC(=O)C(CO)NC(=O)C(CC(=O)O)NC(=O)C(CC(C)C)NC(=O)C(CC4=CC=C(C=C4)O)NC(=O)C(CCCCN)NC(=O)C(CO)NC(=O)C(CC5=CC=C(C=C5)O)NC(=O)C(CC(=O)O)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C(CC6=CC=CC=C6)NC(=O)C(C(C)O)NC(=O)CNC(=O)C(CCC(=O)N)NC(=O)C(CO)NC(=O)C(CC7=CN=CN7)N
    2.1.5 Isomeric SMILES
    C[C@H]([C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CC2=CC=C(C=C2)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC3=CC=C(C=C3)O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CC4=CC=CC=C4)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CC5=CNC6=CC=CC=C65)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H]([C@@H](C)O)C(=O)O)NC(=O)CNC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CO)NC(=O)[C@H](CC7=CN=CN7)N)O
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Big Plasma Glucagon

    2. Glucagon-like-immunoreactivity

    3. Gut Glucagon-like Immunoreactants

    2.2.2 Depositor-Supplied Synonyms

    1. Glucagonum

    2. Glucagone

    3. His-ser-glu(nh2)-gly-thr-phe-thr-ser-asp-tyr-ser-lys-tyr-leu-asp-ser-arg-arg-ala-glu(nh2)-asp-phe-val-glu(nh2)-trp-leu-met-asp(nh2)-thr

    4. Glucagon-like-immunoreactivity

    5. Glucaton

    6. Bovine Glucagon

    7. Glukagon Novo

    8. Glucagon, Pig

    9. Glucagon (dog)

    10. Glucagon (pig)

    11. Glucagon (ox)

    12. Big Plasma Glucagon

    13. Glucagone [dcit]

    14. Glucagonum [inn-latin]

    15. Glucagon (xenopus Laevis)

    16. Glucagon (saimiri Sciureus)

    17. Unii-76la80ig2g

    18. 76la80ig2g

    19. Glucagon (mesocricetus Auratus)

    20. Glucagon, Porcine, For Bioassay

    21. Glucagon [usp:inn:ban:jan]

    22. Schembl15268863

    23. Gut Glucagon-like Immunoreactants

    24. Hsdb 3337

    25. Dtxsid101016809

    26. Glucagon, Porcine, For Immunoassay

    27. Hsqgtftsdyskyldsrraqdfvqwlmnt

    28. Einecs 232-708-2

    29. Ncgc00167140-01

    30. Glucagon, Acetate Salt, >=97.0% (hplc)

    31. Human Glucagon, European Pharmacopoeia (ep) Reference Standard

    32. His-ser-gln-gly-thr-phe-thr-ser-asp-tyr-ser-lys-tyr-leu-asp-ser-arg-arg-ala-gln-asp-phe-val-gln-trp-leu-met-asn-thr

    33. L-histidyl-l-seryl-l-glutaminylglycyl-l-threonyl-l-phenylalanyl-l-threonyl-l-seryl-l-alpha-aspartyl-l-tyrosyl-l-seryl-l-lysyl-l-tyrosyl-l-leucyl-l-alpha-aspartyl-l-seryl-l-arginyl-l-arginyl-l-alanyl-l-glutaminyl-l-alpha-aspartyl-l-phenylalanyl-l-valyl-l-glutaminyl-l-tryptophyl-l-leucyl-l-methionyl-l-asparaginyl-l-threonine

    34. L-threonine, L-histidyl-l-seryl-l-glutaminylglycyl-l-threonyl-l-phenylalanyl-l-threonyl-l-seryl-l-.alpha.-aspartyl-l-tyrosyl-l-seryl-l-lysyl-l-tyrosyl-l-leucyl-l-.alpha.-aspartyl-l-seryl-l-arginyl-l-argin Yl-l-alanyl-l-glutaminyl-l-.alpha.-aspartyl-l-phenylalanyl-l-valyl-l-glutaminyl-l-tryptophyl-l-leucyl-l-methionyl-l-asparaginyl-

    35. L-threonine, L-histidyl-l-seryl-l-glutaminylglycyl-l-threonyl-l-phenylalanyl-l-threonyl-l-seryl-l-alpha-aspartyl-l-tyrosyl-l-seryl-l-lysyl-l-tyrosyl-l-leucyl-l-alpha-aspartyl-l-seryl-l-arginyl-l-arginyl-l-alanyl-l-glytaminyl-l-alpha-aspartyl-l-phenylalanyl-l-valyl-l-glutaminyl-l-tryptophyl-l-leucyl-l-methionyl-l-asparaginyl-

    2.3 Create Date
    2007-07-03
    3 Chemical and Physical Properties
    Molecular Weight 3482.7 g/mol
    Molecular Formula C153H225N43O49S
    XLogP3-16.9
    Hydrogen Bond Donor Count55
    Hydrogen Bond Acceptor Count55
    Rotatable Bond Count115
    Exact Mass3481.6190567 g/mol
    Monoisotopic Mass3480.6157019 g/mol
    Topological Polar Surface Area1560 Ų
    Heavy Atom Count246
    Formal Charge0
    Complexity8160
    Isotope Atom Count0
    Defined Atom Stereocenter Count31
    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

    Gastrointestinal Agents; Protein Synthesis Inhibitors

    National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

    Glucagon is used in the treatment of lower esophageal obstruction due to foreign bodies, including food boluses. /NOT included in US product labeling/

    USP Convention. USPDI-Drug Information for the Health Care Professional. 14th ed. Volume I. Rockville, MD: United States Pharmacopeial Convention, Inc., 1994. (Plus Updates)., p. 1440

    Glucagon may be of use in treating myocardial depression due to calcium channel blocking agents in those patients in whom conventional therapies have been ineffective. /NOT included in US product labeling/

    USP Convention. USPDI-Drug Information for the Health Care Professional. 14th ed. Volume I. Rockville, MD: United States Pharmacopeial Convention, Inc., 1994. (Plus Updates)., p. 1440

    Glucagon administered in large intravenous doses is used to treat the cardiotoxic effects, specifically bradycardia and hypotension, in overdoses of beta-adrenergic blocking agents. Glucagon may be used with the proterenol or dobutamine. Supplemental potassium may be necessary for treated patients since glucagon tends to reduce serum potassium. /NOT included in US product labeling/

    USP Convention. USPDI-Drug Information for the Health Care Professional. 14th ed. Volume I. Rockville, MD: United States Pharmacopeial Convention, Inc., 1994. (Plus Updates)., p. 1440

    For more Therapeutic Uses (Complete) data for GLUCAGON (19 total), please visit the HSDB record page.

    4.2 Drug Warning

    ...EFFECTIVE ONLY WHEN ADMIN PARENTERALLY. ITS HYPERGLYCEMIC EFFECT IS...OF RELATIVELY BRIEF DURATION. .../SUPPLEMENTARY CARBOHYDRATES SHOULD BE GIVEN AS SOON AS POSSIBLE AFTER PATIENT RESPONDS/. AN ADDITIONAL SUGAR SOURCE IS ESPECIALLY IMPORTANT IN JUVENILES...

    American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 1045

    Since glucagon is a protein, the possibility of hypersensitivity reactions should be considered.

    McEvoy, G.K. (ed.). American Hospital Formulary Service--Drug Information 94. Bethesda, MD: American Society of Hospital Pharmacists, Inc. 1994 (Plus Supplements)., p. 2076

    Side/Adverse Effects: Those indicating need for medical attention only if they continue or are bothersome: Nausea or vomiting - incidence is generally dependent upon dose and (with intravenous use) the rate of injection; these effects may be diminished by slower intravenous administration.

    USP Convention. USPDI-Drug Information for the Health Care Professional. 14th ed. Volume I. Rockville, MD: United States Pharmacopeial Convention, Inc., 1994. (Plus Updates)., p. 1441

    Glucagon should not be used to treat birth asphyxia or hypoglycemia in premature infants or in infants who have had intrauterine growth retardation.

    USP Convention. USPDI-Drug Information for the Health Care Professional. 14th ed. Volume I. Rockville, MD: United States Pharmacopeial Convention, Inc., 1994. (Plus Updates)., p. 1440

    Glucagon has been used as an aid in the diagnosis of insulinoma and pheochromocytoma; however, USP advisory panels do not generally recommend this use because of questions about safety.

    USP Convention. USPDI-Drug Information for the Health Care Professional. 14th ed. Volume I. Rockville, MD: United States Pharmacopeial Convention, Inc., 1994. (Plus Updates)., p. 1440

    4.3 Drug Indication

    Glucagon is indicated as a diagnostic aid in radiologic exams to temporarily inhibit the movement of the gastrointestinal tract and to treat severe hypoglycemia.

    FDA Label

    Baqsimi is indicated for the treatment of severe hypoglycaemia in adults, adolescents, and children aged 4 years and over with diabetes mellitus.

    Ogluo is indicated for the treatment of severe hypoglycaemia in adults, adolescents, and children aged 2 years and over with diabetes mellitus.

    Treatment of hypoglycaemia

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Glucagon is indicated as a diagnostic aid in radiologic exams to temporarily inhibit the movement of the gastrointestinal tract and severe hypoglycemia. Glucagon raises blood sugar through activation of hepatic glucagon receptors, stimulating glycogenolysis and the release of glucose. Glucagon has a short duration of action. Glucagon may cause hyperglycemia in diabetic patients.

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Decreased GI Motility [PE]; Decreased GI Smooth Muscle Tone [PE]; Decreased Glycolysis [PE]; Gastrointestinal Motility Inhibitor [EPC]; Increased Gluconeogenesis [PE]; Increased Glycogenolysis [PE]; Antihypoglycemic Agent [EPC]
    5.3 ATC Code

    H04AA01

    H04AA01

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

    H04 - Pancreatic hormones

    H04A - Glycogenolytic hormones

    H04AA - Glycogenolytic hormones

    H04AA01 - Glucagon

    5.4 Absorption, Distribution and Excretion

    Absorption

    A 1mg intravenous dose of glucagon reaches a Cmax of 7.9ng/mL with a Tmax of 20 minutes. An intramuscular dose reaches a Cmax of 6.9ng/mL with a Tmax of 13 minutes. A 3mg dose of glucagon nasal powder reaches a Cmax of 6130pg/mL with a Tmax of 15 minutes.

    Route of Elimination

    Elimination of glucagon is not fully characterized in literature, however the kidney and liver appear to contribute significantly in animal models. The liver and kidney are responsible for approximately 30% of glucagon elimination each.

    Volume of Distribution

    The volume of distribution of glucagon is 0.25L/kg. The apparent volume of distribution is 885L.

    Clearance

    A 1mg intravenous dose of glucagon has a clearance of 13.5mL/min/kg.

    Because of its polypeptide nature, glucagon is destroyed in the GI tract, and therefore must be administered parenterally.

    McEvoy, G.K. (ed.). American Hospital Formulary Service--Drug Information 94. Bethesda, MD: American Society of Hospital Pharmacists, Inc. 1994 (Plus Supplements)., p. 2075

    5.5 Metabolism/Metabolites

    Glucagon is a protein and so it is metabolized into smaller polypeptides and amino acids in the liver, kidney, and plasma.

    5.6 Biological Half-Life

    The half life of glucagon is 26 minutes for an intramuscular dose. The half life of glucagon nasal powder is approximately 35 minutes. The half life of glucagon by a subcutaneous auto-injector or pre-filled syringe is 32 minutes.

    Glucagon has a plasma half-life of about 3-10 minutes.

    McEvoy, G.K. (ed.). American Hospital Formulary Service--Drug Information 94. Bethesda, MD: American Society of Hospital Pharmacists, Inc. 1994 (Plus Supplements)., p. 2075

    5.7 Mechanism of Action

    Glucagon binds to the glucagon receptor activating Gs and Gq. This activation activates adenylate cyclase, which increases intracellular cyclic AMP and activates protein kinase A. Activating Gq activates phospholipase C, increases production of inositol 1,4,5-triphosphate, and releases intracellular calcium. Protein kinase A phosphorylates glycogen phosphorylase kinase, which phosphorylates glycogen phosphorylase, which phosphorylates glycogen, causing its breakdown. Glucagon also relaxes smooth muscle of the stomach, duodenum, small bowel, and colon.

    Glucagon increases the blood glucose concentration by mobilizing hepatic glycogen and thus is effective only when hepatic glycogen is available. Patients with reduced glycogen stores (eg, starvation, adrenal insufficiency, alcoholic hypoglycemia) cannot respond to glucagon.

    American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 1045

    Glucagon produces extra hepatic effects that are independent of its hyperglycemic action. Although the exact mechanism(s) of action has not been conclusively determined, glucagon produces relaxation of smooth muscle of the stomach, duodenum, small intestine, and colon. The drug has also been shown to inhibit gastric and pancreatic secretions.

    McEvoy, G.K. (ed.). American Hospital Formulary Service--Drug Information 94. Bethesda, MD: American Society of Hospital Pharmacists, Inc. 1994 (Plus Supplements)., p. 2075

    Promotes hepatic glycogenolysis and gluconeogenesis. Stimulates adenylate cyclase to produce increased cyclic-AMP, which is involved in a series of enzymatic activities. The resultant effects are increased concentrations of plasma glucose, a relaxant effect on smooth musculature, and an inotropic myocardial effect. Hepatic stores of glycogen are necessary for glucagon to elicit an antihypoglycemic effect.

    USP Convention. USPDI-Drug Information for the Health Care Professional. 14th ed. Volume I. Rockville, MD: United States Pharmacopeial Convention, Inc., 1994. (Plus Updates)., p. 1441

    API Reference Price

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ROAD,","city":"MUMBAI,MAHARASHTRA","supplier":"BACHEM AG","supplierCountry":"SWITZERLAND","foreign_port":"BASEL","customer":"LUPIN LTD","customerCountry":"INDIA","quantity":"0.22","actualQuantity":"220","unit":"GMS","unitRateFc":"5185.5","totalValueFC":"1153807.9","currency":"USD","unitRateINR":"442580.7","date":"26-Nov-2024","totalValueINR":"97367758.4","totalValueInUsd":"1153807.9","indian_port":"M\/s MAHARASHTRA AIRPORT DEVELOPMENTCOMPANYLIMITED","hs_no":"29371900","bill_no":"6893161","productDescription":"API","marketType":"REGULATED MARKET","country":"SWITZERLAND","selfForZScoreResived":"Pharma Grade","supplierPort":"BASEL","supplierAddress":"Hauptstrasse 144 Bubendorf Schweiz SDNF Switzerland","customerAddress":"159, C.S.T. ROAD,"}]
    25-Mar-2021
    26-Nov-2024
    KGS
    overview
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    Average Price (USD/KGS)

    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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