ACTH (2-24) supplier

Tetracosactide acetate

Catalog No.

S11178569

CAS No.

M.F

C136H210N40O31S

M. Wt

2933.4 g/mol

Availability

In Stock

* This item is exclusively intended for research purposes and is not designed for human therapeutic applications or veterinary use.

Content Navigation

• 1. General Information
• 2. Description
• 3. Chemical Reactions
• 4. Biological Activity
• 5. Synthesis Methods
• 6. Applications
• 7. Interaction Studies
• 8. Similar Compounds
• 9.
• 10.
• 11. Specification
• 12. Others

General Information

Product Name

Tetracosactide acetate

IUPAC Name

1-[2-[[2-[[6-amino-2-[[2-[[1-[2-[[2-[[6-amino-2-[[6-amino-2-[[2-[[2-[[1-[6-amino-2-[[2-[[2-[[2-[[2-[[2-[[2-[[2-[[2-[[2-[(2-amino-3-hydroxypropanoyl)amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-hydroxypropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-4-carboxybutanoyl]amino]-3-(1H-imidazol-4-yl)propanoyl]amino]-3-phenylpropanoyl]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

Molecular Formula

C136H210N40O31S

Molecular Weight

2933.4 g/mol

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)

InChI Key

ZOEFCCMDUURGSE-UHFFFAOYSA-N

Canonical SMILES

CC(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(CC2=CC=C(C=C2)O)C(=O)N3CCCC3C(=O)O)NC(=O)C4CCCN4C(=O)C(CCCCN)NC(=O)CNC(=O)C(CC5=CNC6=CC=CC=C65)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC7=CC=CC=C7)NC(=O)C(CC8=CNC=N8)NC(=O)C(CCC(=O)O)NC(=O)C(CCSC)NC(=O)C(CO)NC(=O)C(CC9=CC=C(C=C9)O)NC(=O)C(CO)N

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.

Description

Tetracosactide acetate, also known as Cosyntropin, is a synthetic peptide that mimics the first 24 amino acids of the adrenocorticotropic hormone. Its chemical formula is C138H214N40O33S, and it has a molecular weight of approximately 3293.8 g/mol. This compound is primarily utilized in medical applications to stimulate the adrenal cortex, leading to the secretion of corticosteroids, which are vital in managing various conditions such as adrenal insufficiency and certain autoimmune disorders.

Chemical Reactions

Tetracosactide acetate functions by binding to specific receptors on the surface of adrenal cortical cells. This interaction activates adenylate cyclase, which increases the levels of cyclic adenosine monophosphate (cAMP) in the cells. The elevated cAMP levels promote the conversion of cholesterol to pregnenolone, a precursor for various corticosteroids. The metabolic pathway can be summarized as follows:

• Binding: Tetracosactide binds to the ACTH receptor on adrenal cells.
• Activation: The hormone-receptor complex activates adenylate cyclase.
• cAMP Production: Increased cAMP stimulates steroidogenesis.
• Corticosteroid Release: Pregnenolone is converted into glucocorticoids and mineralocorticoids.

Biological Activity

Tetracosactide acetate exhibits biological activities similar to those of natural adrenocorticotropic hormone. Its primary action is to stimulate the production of glucocorticoids and mineralocorticoids from the adrenal cortex, which are crucial for regulating metabolism, immune response, and stress reactions. Additionally, it has been shown to have a prolonged effect compared to natural corticotropin, allowing for less frequent administration in therapeutic settings.

Synthesis Methods

The synthesis of tetracosactide acetate typically involves solid-phase peptide synthesis techniques. This method allows for the sequential addition of amino acids to form the desired peptide chain. The process can be summarized in several steps:

• Preparation: A solid support is functionalized with an amino acid.
• Coupling: Protected amino acids are sequentially coupled to form peptide bonds.
• Deprotection: Protective groups are removed after each coupling step.
• Cleavage: The completed peptide is cleaved from the solid support.
• Purification: The crude product is purified using techniques such as high-performance liquid chromatography.

The final product is then acetylated to form tetracosactide acetate, enhancing its stability and bioavailability.

Applications

Tetracosactide acetate has several clinical applications:

• Diagnostic Testing: It is used in diagnostic tests for assessing adrenal function by measuring cortisol response after administration.
• Therapeutic Use: It serves as an alternative treatment for conditions like Crohn's disease and rheumatoid arthritis, particularly in patients who cannot tolerate oral glucocorticoids.
• Hormonal Replacement Therapy: It may be used in cases of adrenal insufficiency to replace deficient hormones.

Interaction Studies

Research indicates that tetracosactide acetate can interact with various medications, potentially increasing hepatotoxicity when combined with agents like clonazepam. Additionally, it may influence the pharmacokinetics of other drugs metabolized by hepatic enzymes due to its effects on glucocorticoid levels.

Similar Compounds

Tetracosactide acetate shares structural and functional similarities with several other peptides and hormones involved in adrenal function and steroidogenesis. Here are some comparable compounds:

Tetracosactide acetate's uniqueness lies in its specific action on adrenal steroidogenesis while being a synthetic ana