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    Chemistry

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    Also known as: Pramlintide acetate [usan], Schembl238214, Unii-726i6te06g, Aco137, 726i6te06g, 25-l-proline-28-l-proline-29-l-proline-, acetate (salt), hydrate
    Molecular Formula
    C171H269N51O53S2
    Molecular Weight
    3951  g/mol
    InChI Key
    NRKVKVQDUCJPIZ-MKAGXXMWSA-N
    Pramlintide
    Pramlintide Acetate is the acetate salt form of pramlintide, a peptide analogue of human amylin with 3 proline substitutions at position 25, 28 and 29, with antihyperglycemic activity. By mimicking amylin, pramlintide slows gastric emptying, inhibits digestive secretions (gastric acid, pancreatic enzymes, and bile), reduces glucagon secretion, and increases satiety; all of these actions are mediated mostly by glucose-sensitive areas in the brain stem. The overall result is a decrease in blood glucose levels. The use of pramlintide may cause an increased risk of insulin-induced hypoglycemia.
    1 2D Structure

    Pramlintide

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-4-amino-1-[[(2S)-1-[[2-[(2S)-2-[[(2S,3S)-1-[[(2S)-1-[(2S)-2-[(2S)-2-[[(2S,3R)-1-[[(2S)-4-amino-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-4-amino-1-[[(2S,3R)-1-[[(2S)-1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]carbamoyl]pyrrolidine-1-carbonyl]pyrrolidin-1-yl]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-2-oxoethyl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]-2-[[(2S,3R)-2-[[(2S)-2-[[(2R)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-4-amino-2-[[(2R)-2-[[(2S)-2,6-diaminohexanoyl]amino]-3-sulfanylpropanoyl]amino]-4-oxobutanoyl]amino]-3-hydroxybutanoyl]amino]propanoyl]amino]-3-hydroxybutanoyl]amino]-3-sulfanylpropanoyl]amino]propanoyl]amino]-3-hydroxybutanoyl]amino]pentanediamide
    2.1.2 InChI
    InChI=1S/C171H269N51O53S2/c1-21-81(12)130(163(268)207-110(56-78(6)7)169(274)222-53-33-42-118(222)170(275)221-52-32-41-117(221)160(265)219-135(89(20)230)167(272)206-109(66-125(180)238)151(256)212-128(79(8)9)161(266)186-68-126(239)192-111(70-223)154(259)203-107(64-123(178)236)152(257)218-134(88(19)229)166(271)195-98(136(181)241)57-92-43-45-94(231)46-44-92)214-159(264)116-40-31-51-220(116)127(240)69-187-141(246)101(58-90-34-24-22-25-35-90)199-148(253)105(62-121(176)234)201-149(254)106(63-122(177)235)202-155(260)112(71-224)209-156(261)113(72-225)208-146(251)103(60-93-67-184-75-188-93)205-162(267)129(80(10)11)213-150(255)100(55-77(4)5)198-145(250)102(59-91-36-26-23-27-37-91)200-147(252)104(61-120(175)233)196-137(242)82(13)189-144(249)99(54-76(2)3)197-142(247)96(39-30-50-185-171(182)183)193-143(248)97(47-48-119(174)232)194-165(270)132(86(17)227)215-138(243)83(14)190-157(262)114(73-276)211-168(273)133(87(18)228)216-139(244)84(15)191-164(269)131(85(16)226)217-153(258)108(65-124(179)237)204-158(263)115(74-277)210-140(245)95(173)38-28-29-49-172/h22-27,34-37,43-46,67,75-89,95-118,128-135,223-231,276-277H,21,28-33,38-42,47-66,68-74,172-173H2,1-20H3,(H2,174,232)(H2,175,233)(H2,176,234)(H2,177,235)(H2,178,236)(H2,179,237)(H2,180,238)(H2,181,241)(H,184,188)(H,186,266)(H,187,246)(H,189,249)(H,190,262)(H,191,269)(H,192,239)(H,193,248)(H,194,270)(H,195,271)(H,196,242)(H,197,247)(H,198,250)(H,199,253)(H,200,252)(H,201,254)(H,202,260)(H,203,259)(H,204,263)(H,205,267)(H,206,272)(H,207,268)(H,208,251)(H,209,261)(H,210,245)(H,211,273)(H,212,256)(H,213,255)(H,214,264)(H,215,243)(H,216,244)(H,217,258)(H,218,257)(H,219,265)(H4,182,183,185)/t81-,82-,83-,84-,85+,86+,87+,88+,89+,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,128-,129-,130-,131-,132-,133-,134-,135-/m0/s1
    2.1.3 InChI Key
    NRKVKVQDUCJPIZ-MKAGXXMWSA-N
    2.1.4 Canonical SMILES
    CCC(C)C(C(=O)NC(CC(C)C)C(=O)N1CCCC1C(=O)N2CCCC2C(=O)NC(C(C)O)C(=O)NC(CC(=O)N)C(=O)NC(C(C)C)C(=O)NCC(=O)NC(CO)C(=O)NC(CC(=O)N)C(=O)NC(C(C)O)C(=O)NC(CC3=CC=C(C=C3)O)C(=O)N)NC(=O)C4CCCN4C(=O)CNC(=O)C(CC5=CC=CC=C5)NC(=O)C(CC(=O)N)NC(=O)C(CC(=O)N)NC(=O)C(CO)NC(=O)C(CO)NC(=O)C(CC6=CN=CN6)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC7=CC=CC=C7)NC(=O)C(CC(=O)N)NC(=O)C(C)NC(=O)C(CC(C)C)NC(=O)C(CCCNC(=N)N)NC(=O)C(CCC(=O)N)NC(=O)C(C(C)O)NC(=O)C(C)NC(=O)C(CS)NC(=O)C(C(C)O)NC(=O)C(C)NC(=O)C(C(C)O)NC(=O)C(CC(=O)N)NC(=O)C(CS)NC(=O)C(CCCCN)N
    2.1.5 Isomeric SMILES
    CC[C@H](C)[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N1CCC[C@H]1C(=O)N2CCC[C@H]2C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC3=CC=C(C=C3)O)C(=O)N)NC(=O)[C@@H]4CCCN4C(=O)CNC(=O)[C@H](CC5=CC=CC=C5)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CC6=CN=CN6)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC7=CC=CC=C7)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](C)NC(=O)[C@H](CS)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CS)NC(=O)[C@H](CCCCN)N
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Ac 0137

    2. Ac 137

    3. Lys-cys-asn-thr-ala-thr-cys-ala-thr-gln-arg-leu-ala-asn-phe-leu-val-his-ser-ser-asn-asn-phe-gly-pro-ile-leu-pro-pro-thr-asn-val-gly-ser-asn-thr-tyr-nh2

    4. Pramlintide

    5. Pramlintide Acetate

    6. Tripro-amylin

    2.2.2 Depositor-Supplied Synonyms

    1. Pramlintide Acetate [usan]

    2. Schembl238214

    3. Unii-726i6te06g

    4. Aco137

    5. 726i6te06g

    6. 25-l-proline-28-l-proline-29-l-proline-, Acetate (salt), Hydrate

    7. 25-l-proline-28-l-proline-29-l-prolineamylin (human) Acetate (salt), Hydrate

    2.3 Create Date
    2007-07-03
    3 Chemical and Physical Properties
    Molecular Weight 3951 g/mol
    Molecular Formula C171H269N51O53S2
    XLogP3-16.7
    Hydrogen Bond Donor Count58
    Hydrogen Bond Acceptor Count59
    Rotatable Bond Count122
    Exact Mass3949.9396798 g/mol
    Monoisotopic Mass3948.9363250 g/mol
    Topological Polar Surface Area1690 Ų
    Heavy Atom Count277
    Formal Charge0
    Complexity9620
    Isotope Atom Count0
    Defined Atom Stereocenter Count41
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameSymlin
    PubMed HealthPramlintide (Injection)
    Drug ClassesAntidiabetic
    Active IngredientPramlintide acetate
    Dosage FormInjectable
    RouteSubcutaneous
    Strengtheq 1.5mg base/1.5ml (eq 1mg base/ml); eq 2.7mg base/2.7ml (eq 1mg base/ml)
    Market StatusPrescription
    CompanyAstrazeneca Ab

    2 of 2  
    Drug NameSymlin
    PubMed HealthPramlintide (Injection)
    Drug ClassesAntidiabetic
    Active IngredientPramlintide acetate
    Dosage FormInjectable
    RouteSubcutaneous
    Strengtheq 1.5mg base/1.5ml (eq 1mg base/ml); eq 2.7mg base/2.7ml (eq 1mg base/ml)
    Market StatusPrescription
    CompanyAstrazeneca Ab

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Hypoglycemic Agents

    Substances which lower blood glucose levels. (See all compounds classified as Hypoglycemic Agents.)

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    DOSAGE - INJECTABLE;SUBCUTANEOUS - EQ 1.5MG B...DOSAGE - INJECTABLE;SUBCUTANEOUS - EQ 1.5MG BASE/1.5ML (EQ 1MG BASE/ML)

    USFDA APPLICATION NUMBER - 21332

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    DOSAGE - INJECTABLE;SUBCUTANEOUS - EQ 2.7MG B...DOSAGE - INJECTABLE;SUBCUTANEOUS - EQ 2.7MG BASE/2.7ML (EQ 1MG BASE/ML)

    USFDA APPLICATION NUMBER - 21332

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