Tetracosactide
Identification
- Name
- Tetracosactide
- Accession Number
- DB01284
- Type
- Small Molecule
- Groups
- Approved
- Description
Tetracosactide (also known as Cosyntropin) is a synthetic peptide that is identical to the 24-amino acid segment (sequence: SYSMEHFRWGKPVGKKRRPVKVYP) 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. Tetracosactide exhibits the same activity as natural ACTH with regard to all its biological activities. The complex results in a product whose absorption in man is effected over a longer period of time as compared to corticotropin. Therefore, therapy may be maintained with less frequent administration.
- Structure
Structure for Tetracosactide (DB01284)
- Synonyms
- adrenocorticotropic hormone 1-24
- Adrenocorticotropic hormone fragment 1-24 human, rat
- alpha(1-24)-corticotrophin
- ATCH (1-24)
- beta(1-24)-corticotrophin
- Corticotropin tetracosapeptide
- corticotropin-(1-24)
- corticotropin-(1-24) tetracosapeptide
- Cosyntropin
- Tetracosactida
- Tetracosactide
- Tetracosactrin
- α1-24-corticotrophin
- β1-24-corticotrophin
- Product Ingredients
Ingredient UNII CAS InChI Key Tetracosactide acetate H86HJ92K8Y 22633-88-1 DFABUZLKSKOWCS-WMPFGLIOSA-N - Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataCortrosyn Injection, powder, lyophilized, for solution 0.25 mg/1mL Intramuscular; Intravenous A-S Medication Solutions 2003-08-01 Not applicable US 
Cortrosyn Injection, powder, lyophilized, for solution 0.25 mg/1mL Intramuscular; Intravenous; Parenteral General Injectables & Vaccines, Inc 2010-03-01 Not applicable US Cortrosyn Injection, powder, lyophilized, for solution 0.25 mg/1mL Intramuscular; Intravenous Amphastar Pharmaceuticals, Inc. 2003-08-01 Not applicable US Cortrosyn Inj 0.25mg Powder, for solution Intramuscular; Intravenous Amphastar Pharmaceuticals, Inc. 1974-12-31 Not applicable Canada 
Cosyntropin Injection, solution 0.25 mg/1mL Intravenous Sandoz 2008-02-21 2011-12-31 US Synacthen Depot Suspension Intramuscular Mallinckrodt Specialty Pharmaceuticals Ireland Ltd. 1973-12-31 Not applicable Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataCosyntropin Injection, powder, lyophilized, for solution 0.25 mg/1mL Intramuscular; Intravenous GeneraMedix 2009-12-18 2013-02-08 US Cosyntropin Injection, powder, lyophilized, for solution 0.25 mg/1mL Intravenous Sandoz Inc 2012-06-29 Not applicable US Cosyntropin Injection, powder, for solution 0.25 mg/1mL Intramuscular; Intravenous Mylan Institutional LLC 2013-04-24 Not applicable US Cosyntropin Injection, powder, for solution 0.25 mg/1mL Intramuscular; Intravenous Mylan Institutional LLC 2012-07-27 2012-07-27 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
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A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Categories
- Adrenals
- Adrenocortical Insufficiency
- Adrenocorticotropic Hormone
- Amino Acids, Peptides, and Proteins
- Anterior Pituitary Lobe Hormones and Analogues
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Melanocortins
- Nerve Tissue Proteins
- Neuropeptides
- Peptide Hormones
- Peptides
- Pituitary
- Pituitary and Hypothalamic Hormones and Analogues
- Pituitary Hormones
- Pituitary Hormones, Anterior
- Pro-Opiomelanocortin
- Protein Precursors
- Proteins
- Systemic Hormonal Preparations, Excl. Sex Hormones and Insulins
- UNII
- 72YY86EA29
- CAS number
- 16960-16-0
- Weight
- Average: 2933.49
Monoisotopic: 2931.580641316 - Chemical Formula
- C136H210N40O31S
- InChI Key
- ZOEFCCMDUURGSE-SQKVDDBVSA-N
- InChI
- InChI=1S/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-/m0/s1
- IUPAC Name
- (2S)-1-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-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-[(2S)-2-amino-3-hydroxypropanamido]-3-(4-hydroxyphenyl)propanamido]-3-hydroxypropanamido]-4-(methylsulfanyl)butanamido]-4-carboxybutanamido]-3-(1H-imidazol-5-yl)propanamido]-3-phenylpropanamido]-5-carbamimidamidopentanamido]-3-(1H-indol-3-yl)propanamido]acetamido}hexanoyl]pyrrolidin-2-yl]formamido}-3-methylbutanamido]acetamido}hexanamido]hexanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}-3-methylbutanamido]hexanamido]-3-methylbutanamido]-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carboxylic acid
- 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=CN=CN1)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
Pharmacology
- Indication
For use as a diagnostic agent in the screening of patients presumed to have adrenocortical insufficiency.
- Associated Conditions
- Acute Gouty Arthritis
- Acute Rheumatic Fever
- Adrenal Insufficiency
- Ankylosing Spondylitis (AS)
- Bell's Palsy
- Choroiditis
- Conjunctivitis
- Corneal Inflammation
- Dermatitis exfoliative generalised
- Dermatomyositis
- Iritis
- Lupus Erythematosus
- Multiple sclerosis exacerbation
- Nephrotic Syndrome
- Ophthalmia, Sympathetic
- Optic Neuritis
- Panhypopituitarism
- Pemphigus
- Periarteritis nodosa
- Psoriatic Arthritis
- Rheumatoid Arthritis
- Scleroderma
- Still's Disease
- Ulcerative Colitis
- Uveitis
- Acquired hemolytic jaundice
- Pharmacodynamics
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.
Target Actions Organism AAdrenocorticotropic hormone receptor antagonistHumans - Absorption
Rapidly absorbed following intramuscular administration.
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
- Not Available
- Route of elimination
- Not Available
- Half life
About 15 minutes following intravenous administration.
- Clearance
- Not Available
- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.
Learn moreStructured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.
Learn moreStructured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.
Learn moreInteractions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional Data7-Nitroindazole The risk or severity of liver damage can be increased when Tetracosactide is combined with 7-Nitroindazole. Acetazolamide The risk or severity of liver damage can be increased when Tetracosactide is combined with Acetazolamide. Amobarbital The risk or severity of liver damage can be increased when Tetracosactide is combined with Amobarbital. Barbexaclone The risk or severity of liver damage can be increased when Tetracosactide is combined with Barbexaclone. Barbital The risk or severity of liver damage can be increased when Tetracosactide is combined with Barbital. Beclamide The risk or severity of liver damage can be increased when Tetracosactide is combined with Beclamide. Brexanolone The risk or severity of liver damage can be increased when Tetracosactide is combined with Brexanolone. Brivaracetam The risk or severity of liver damage can be increased when Tetracosactide is combined with Brivaracetam. Butalbital The risk or severity of liver damage can be increased when Tetracosactide is combined with Butalbital. Cannabidiol The risk or severity of liver damage can be increased when Tetracosactide is combined with Cannabidiol. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
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- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
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- Food Interactions
- Not Available
References
- General References
- Not Available
- External Links
- KEGG Drug
- D00284
- KEGG Compound
- C06926
- PubChem Compound
- 16133751
- PubChem Substance
- 46506301
- ChemSpider
- 10481947
- BindingDB
- 50017180
- ChEBI
- 3901
- ChEMBL
- CHEMBL2103784
- Therapeutic Targets Database
- DAP000284
- PharmGKB
- PA164749052
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Tetracosactide
- ATC Codes
- H01AA02 — Tetracosactide
- AHFS Codes
- 68:04.00 — Adrenals
- 36:04.00 — Adrenocortical Insufficiency
- 68:28.00 — Pituitary
Clinical Trials
- Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Amphastar Pharmaceuticals
- Generamedix Inc.
- Sandoz
- Dosage forms
Form Route Strength Injection, powder, lyophilized, for solution Intramuscular; Intravenous; Parenteral 0.25 mg/1mL Powder, for solution Intramuscular; Intravenous Injection, powder, for solution Intramuscular; Intravenous 0.25 mg/1mL Injection, powder, lyophilized, for solution Intramuscular; Intravenous 0.25 mg/1mL Injection, powder, lyophilized, for solution Intravenous 0.25 mg/1mL Injection, solution Intravenous 0.25 mg/1mL Suspension Intramuscular - Prices
Unit description Cost Unit Cortrosyn 0.25 mg vial 127.9USD vial Cosyntropin 0.25 mg/ml 119.91USD ml Cosyntropin 0.25 mg vial 115.1USD vial Synacthen Depot 1 mg/vial 34.77USD vial DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0481 mg/mL ALOGPS logP -0.95 ALOGPS logP -14 ChemAxon logS -4.8 ALOGPS pKa (Strongest Acidic) 3.03 ChemAxon pKa (Strongest Basic) 12.38 ChemAxon Physiological Charge 6 ChemAxon Hydrogen Acceptor Count 46 ChemAxon Hydrogen Donor Count 42 ChemAxon Polar Surface Area 1158.72 Å2 ChemAxon Rotatable Bond Count 93 ChemAxon Refractivity 790.98 m3·mol-1 ChemAxon Polarizability 309.35 Å3 ChemAxon Number of Rings 9 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues.
- Kingdom
- Organic compounds
- Super Class
- Organic Polymers
- Class
- Polypeptides
- Sub Class
- Not Available
- Direct Parent
- Polypeptides
- Alternative Parents
- Peptides / Tyrosine and derivatives / Arginine and derivatives / Phenylalanine and derivatives / Histidine and derivatives / Glutamic acid and derivatives / Methionine and derivatives / Valine and derivatives / Proline and derivatives / N-acyl-L-alpha-amino acids show 30 more
- Substituents
- Polypeptide / Alpha peptide / Tyrosine or derivatives / Arginine or derivatives / Phenylalanine or derivatives / Histidine or derivatives / Glutamic acid or derivatives / Methionine or derivatives / N-acyl-alpha amino acid or derivatives / N-acyl-alpha-amino acid show 61 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- polypeptide (CHEBI:3901)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Melanocortin receptor activity
- Specific Function
- Receptor for corticotropin (ACTH). This receptor is mediated by G proteins (G(s)) which activate adenylate cyclase (cAMP).
- Gene Name
- MC2R
- Uniprot ID
- Q01718
- Uniprot Name
- Adrenocorticotropic hormone receptor
- Molecular Weight
- 33926.28 Da
References
- 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:15710205]
- Mehrabani PA, Bassett JR: Adrenocorticotropin binding sites in rat cardiac tissue. Pharmacol Biochem Behav. 1990 Jan;35(1):99-103. [PubMed:2156274]
- Moraes RB, Czepielewski MA, Friedman G: Cortisol variation after low-dose Cortrosyn test. Crit Care Med. 2010 Jul;38(7):1612-3. doi: 10.1097/CCM.0b013e3181da4ef1. [PubMed:20562554]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Drug created on May 23, 2007 21:46 / Updated on January 26, 2020 14:39