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Showing drug card for Cosyntropin (DB01284)

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Creation Date 2007-05-24 03:46:02
Update Date 2009-02-19 16:03:36
Primary Accession Number DB01284
Secondary Accession Number Not Available
Name Cosyntropin
Drug Type
  • Approved
  • Biotech
Description A synthetic peptide that is identical to the 24-amino acid segment at the N-terminal of adrenocorticotropic hormone. ACTH (1-24), a segment similar in all species, contains the biological activity that stimulates production of corticosteroids in the adrenal cortex.
Synonyms
  1. Tetracosactide
Brand Names
  1. Cortrosyn
  2. Synacthen depot
Brand Mixtures Not Available
Chemical IUPAC Name (2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-1-[(2R)-2-[[(2R)-2-[[(2R)-6-amino-2-[[(2R)-6-amino-2-[[2-[[(2S)-2-[[(2S)-1-[(2S)-6-amino-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[(2-amino-3-hydroxypropanoyl)amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-hydroxypropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-5-hydroxy-5-oxopentanoyl]amino]-3-(1H-imidazol-4-yl)propanoyl]amino]-3-cyclohexylpropanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]acetyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]acetyl]amino]hexanoyl]amino]hexanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]hexanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carboxylic acid
Chemical Formula C136H210N40O31S
Chemical Structure Structure
Protein Sequence(s) >ACTH(1-24) 
SYSMEHFRWGKPVGKKRRPVKVYP
CAS Registry Number 16960-16-0
InChI Identifier InChI=1/C136H210N40O31S/c1-75(2)109(127(200)154-71-106(181)156-88(31-13-17-52-137)114(187)158-89(32-14-18-53-138)115(188)159-91(35-21-56-149-134(142)143)116(189)164-96(37-23-58-151-136(146)147)131(204)175-60-25-39-104(175)126(199)173-111(77(5)6)128(201)163-90(33-15-19-54-139)120(193)171-110(76(3)4)129(202)169-101(65-80-43-47-84(180)48-44-80)132(205)176-61-26-40-105(176)133(206)207)172-125(198)103-38-24-59-174(103)130(203)95(34-16-20-55-140)157-107(182)70-153-113(186)99(66-81-68-152-87-30-12-11-29-85(81)87)167-117(190)92(36-22-57-150-135(144)145)160-121(194)98(63-78-27-9-8-10-28-78)166-123(196)100(67-82-69-148-74-155-82)168-118(191)93(49-50-108(183)184)161-119(192)94(51-62-208-7)162-124(197)102(73-178)170-122(195)97(165-112(185)86(141)72-177)64-79-41-45-83(179)46-42-79/h8-12,27-30,41-48,68-69,74-77,86,88-105,109-111,152,177-180H,13-26,31-40,49-67,70-73,137-141H2,1-7H3,(H,148,155)(H,153,186)(H,154,200)(H,156,181)(H,157,182)(H,158,187)(H,159,188)(H,160,194)(H,161,192)(H,162,197)(H,163,201)(H,164,189)(H,165,185)(H,166,196)(H,167,190)(H,168,191)(H,169,202)(H,170,195)(H,171,193)(H,172,198)(H,173,199)(H,183,184)(H,206,207)(H4,142,143,149)(H4,144,145,150)(H4,146,147,151)/t86?,88-,89-,90+,91-,92+,93+,94+,95+,96-,97+,98+,99+,100+,101+,102+,103+,104+,105+,109+,110+,111+/m1/s1/f/h142,144,146,148-151,153-154,156-173,183,206H,143,145,147H2
InChI Key ZOEFCCMDUURGSE-MDHHKIBEDM
KEGG Drug D00284 Link Image
KEGG Compound C06926 Link Image
PubChem Compound 16129617 Link Image
PubChem Substance 7847350 Link Image
ChEBI ID Not Available
PharmGKB ID PA449132 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 00022381 Link Image
RxList Link http://www.rxlist.com/cgi/generic/cortrosyn.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Cosyntropin Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 2933.4370
Monoisotopic Molecular Weight 2931.5806
State Solid
Melting Point Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 4.83e-02 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP -0.91 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -4.78 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CSCC[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@H](N)CO)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC1=CNC=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@H](CCCCN)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CCCNC(N)=N)C(=O)N[C@H](CCCNC(N)=N)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC1=CC=C(O)C=C1)C(=O)N1CCC[C@H]1C(O)=O
Canonical SMILES CSCCC(NC(=O)C(CO)NC(=O)C(CC1=CC=C(O)C=C1)NC(=O)C(N)CO)C(=O)NC(CCC(O)=O)C(=O)NC(CC1=CNC=N1)C(=O)NC(CC1=CC=CC=C1)C(=O)NC(CCCNC(N)=N)C(=O)NC(CC1=CNC2=C1C=CC=C2)C(=O)NCC(=O)NC(CCCCN)C(=O)N1CCCC1C(=O)NC(C(C)C)C(=O)NCC(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC(CCCNC(N)=N)C(=O)NC(CCCNC(N)=N)C(=O)N1CCCC1C(=O)NC(C(C)C)C(=O)NC(CCCCN)C(=O)NC(C(C)C)C(=O)NC(CC1=CC=C(O)C=C1)C(=O)N1CCCC1C(O)=O
Drug Category
  • Diagnostic Agents
ATC Codes
AHFS Codes
  • 68:28.00
Indication For use as a diagnostic agent in the screening of patients presumed to have adrenocortical insufficiency.
Pharmacology Cosyntropin exhibits the full corticosteroidogenic activity of natural ACTH. Various studies have shown that the biologic activity of ACTH resides in the N- terminal portion of the molecule and that the 1-20 amino acid residue is the minimal sequence retaining full activity. Partial or complete loss of activity is noted with progressive shortening of the chain beyond 20 amino acid residue. For example, the decrement from 20 to 19 results in a 70% loss of potency. The pharmacologic profile of Cosyntropin is similar to that of purified natural ACTH. It has been established that 0.25 mg of Cosyntropin will stimulate the adrenal cortex maximally and to the same extent as 25 units of natural ACTH. Cosyntropin has less immunogenic activity than ACTH because the amino acid sequence having most of the antigenic activity of ACTH, i.e., amino acids 25-39, is not present in cosyntropin. The extra-adrenal effects which natural ACTH and Cosyntropin have in common include increased melanotropic activity, increased growth hormone secretion and an adipokinetic effect. These are considered to be without physiological or clinical significance.
Mechanism of Action Cosyntropin combines with a specific receptor in the adrenal cell plasma membrane and, in patients with normal adrenocortical function, stimulates the initial reaction involved in the synthesis of adrenal steroids (including cortisol, cortisone, weak androgenic substances, and a limited quantity of aldosterone) from cholesterol by increasing the quantity of the substrate within the mitochondria. Cosyntropin does not significantly increase plasma cortisol concentration in patients with primary or secondary adrenocortical insufficiency.
Absorption Rapidly absorbed following intramuscular administration.
Toxicity Not Available
Protein Binding Not Available
Biotransformation Not Available
Half Life About 15 minutes following intravenous administration.
Dosage Forms
Form Route
Liquid Intramuscular
Powder, for solution Intravenous
Patient Information Not Available
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Wikipedia Link Image
  2. RxList Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. Adrenocorticotropic hormone receptor
Drug Target 1 [top]
Target 1 ID 945
Target 1 Name Adrenocorticotropic hormone receptor
Target 1 Synonyms
  1. ACTH receptor
  2. ACTH-R
  3. Adrenocorticotropin receptor
  4. MC2-R
  5. Melanocortin receptor 2
Target 1 Gene Name MC2R
Target 1 Protein Sequence >Adrenocorticotropic hormone receptor 
MKHIINSYENINNTARNNSDCPRVVLPEEIFFTISIVGVLENLIVLLAVFKNKNLQAPMY
FFICSLAISDMLGSLYKILENILIILRNMGYLKPRGSFETTADDIIDSLFVLSLLGSIFS
LSVIAADRYITIFHALRYHSIVTMRRTVVVLTVIWTFCTGTGITMVIFSHHVPTVITFTS
LFPLMLVFILCLYVHMFLLARSHTRKISTLPRANMKGAITLTILLGVFIFCWAPFVLHVL
LMTFCPSNPYCACYMSLFQVNGMLIMCNAVIDPFIYAFRSPELRDAFKKMIFCSRYW
Target 1 Number of Residues 301
Target 1 Molecular Weight 33927
Target 1 Theoretical pI 8.82
Target 1 GO Classification
Function
signal transducer activity
receptor activity
transmembrane receptor activity
G-protein coupled receptor activity
rhodopsin-like receptor activity
peptide receptor activity, G-protein coupled
melanocortin receptor activity
adrenocorticotropin receptor activity
Process
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
G-protein coupled receptor protein signaling pathway
Component
cell
membrane
intrinsic to membrane
integral to membrane
Target 1 General Function Involved in adrenocorticotropin receptor activity
Target 1 Specific Function Receptor for ACTH. This receptor is mediated by G proteins (G(s)) which activate adenylate cyclase
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 24-49
  • 59-79
  • 105-126
  • 148-168
  • 181-199
  • 218-244
  • 257-278
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 28344 Link Image
Target 1 UniProtKB/Swiss-Prot ID Q01718 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name ACTHR_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >894 bp 
ATGAAGCACATTATCAACTCGTATGAAAACATCAACAACACAGCAAGAAATAATTCCGAC
TGTCCTCGTGTGGTTTTGCCGGAGGAGATATTTTTCACAATTTCCATTGTTGGAGTTTTG
GAGAATCTGATCGTCCTGCTGGCTGTGTTCAAGAATAAGAATCTCCAGGCACCCATGTAC
TTTTTCATCTGTAGCTTGGCCATATCTGATATGCTGGGCAGCCTATATAAGATCTTGGAA
AATATCCTGATCATATTGAGAAACATGGGCTATCTCAAGCCACGTGGCAGTTTTGAAACC
ACAGCCGATGACATCATCGACTCCCTGTTTGTCCTCTCCCTGCTTGGCTCCATCTTCAGC
CTGTCTGTGATTGCTGCGGACCGCTACATCACCATCTTCCACGCACTGCGGTACCACAGC
ATCGTGACCATGCGCCGCACTGTGGTGGTGCTTACGGTCATCTGGACGTTCTGCACGGGG
ACTGGCATCACCATGGTGATCTTCTCCCATCATGTGCCCACAGTGATCACCTTCACGTCG
CTGTTCCCGCTGATGCTGGTCTTCATCCTGTGCCTCTATGTGCACATGTTCCTGCTGGCT
CGATCCCACACCAGGAAGATCTCCACCCTCCCCAGAGCCAACATGAAAGGGGCCATCACA
CTGACCATCCTGCTCGGGGTCTTCATCTTCTGCTGGGCCCCCTTTGTGCTTCATGTCCTC
TTGATGACATTCTGCCCAAGTAACCCCTACTGCGCCTGCTACATGTCTCTCTTCCAGGTG
AACGGCATGTTGATCATGTGCAATGCCGTCATTGACCCCTTCATATATGCCTTCCGGAGC
CCAGAGCTCAGGGACGCATTCAAAAAGATGATCTTCTGCAGCAGGTACTGGTAG
Target 1 GenBank Gene ID
Target 1 GeneCard ID MC2R Link Image
Target 1 GenAtlas ID MC2R Link Image
Target 1 HGNC ID HGNC:6930 Link Image
Target 1 Chromosome Location 18
Target 1 Locus 18p11.2
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Ishii T, Ogata T, Sasaki G, Sato S, Kinoshita EI, Matsuo N: Novel mutations of the ACTH receptor gene in a female adult patient with adrenal unresponsiveness to ACTH. Clin Endocrinol (Oxf). 2000 Sep;53(3):389-92. [PubMed Link Image]
  2. Fluck CE, Martens JW, Conte FA, Miller WL: Clinical, genetic, and functional characterization of adrenocorticotropin receptor mutations using a novel receptor assay. J Clin Endocrinol Metab. 2002 Sep;87(9):4318-23. [PubMed Link Image]
  3. Mountjoy KG, Robbins LS, Mortrud MT, Cone RD: The cloning of a family of genes that encode the melanocortin receptors. Science. 1992 Aug 28;257(5074):1248-51. [PubMed Link Image]
  4. Clark AJ, McLoughlin L, Grossman A: Familial glucocorticoid deficiency associated with point mutation in the adrenocorticotropin receptor. Lancet. 1993 Feb 20;341(8843):461-2. [PubMed Link Image]
  5. Tsigos C, Arai K, Hung W, Chrousos GP: Hereditary isolated glucocorticoid deficiency is associated with abnormalities of the adrenocorticotropin receptor gene. J Clin Invest. 1993 Nov;92(5):2458-61. [PubMed Link Image]
  6. Gantz I, Konda Y, Tashiro T, Shimoto Y, Miwa H, Munzert G, Watson SJ, DelValle J, Yamada T: Molecular cloning of a novel melanocortin receptor. J Biol Chem. 1993 Apr 15;268(11):8246-50. [PubMed Link Image]
  7. Naville D, Barjhoux L, Jaillard C, Faury D, Despert F, Esteva B, Durand P, Saez JM, Begeot M: Demonstration by transfection studies that mutations in the adrenocorticotropin receptor gene are one cause of the hereditary syndrome of glucocorticoid deficiency. J Clin Endocrinol Metab. 1996 Apr;81(4):1442-8. [PubMed Link Image]
Target 1 Drug References
  1. Schwerin M, Kanitz E, Tuchscherer M, Brussow KP, Nurnberg G, Otten W: Stress-related gene expression in brain and adrenal gland of porcine fetuses and neonates. Theriogenology. 2005 Mar 1;63(4):1220-34. [PubMed Link Image]

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