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Application Area

Ostabolin

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Category

Others

Catalog number

BAT-014995

CAS number

173833-08-4

Molecular Formula

C162H270N50O46S2

Molecular Weight

3718.30

Specification
Reference Reading

IUPAC Name

(4S)-4-amino-5-[[(2S)-1-[[(2S)-1-[[(2S)-5-[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-hydroxypropanoyl]amino]-3-methylbutanoyl]amino]-3-hydroxypropanoyl]amino]-4-carboxybutanoyl]amino]-3-methylpentanoyl]amino]-5-oxopentanoyl]amino]-4-methylpentanoyl]amino]-4-methylsulfanylbutanoyl]amino]-3-(4H-imidazol-4-yl)propanoyl]amino]-4-oxobutanoyl]amino]-4-methylpentanoyl]amino]acetyl]amino]hexanoyl]amino]-3-(4H-imidazol-4-yl)propanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-3-hydroxypropanoyl]amino]-4-methylsulfanylbutanoyl]oxy-1-[[(2S)-1-[[(2S)-1-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-amino-5-carbamimidamidopentanoyl]amino]hexanoyl]amino]hexanoyl]amino]-4-methylpentanoyl]amino]-5-oxopentanoyl]amino]-3-carboxypropanoyl]amino]-3-methylbutanoyl]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]-5-carbamimidamido-1-oxopentan-2-yl]amino]-5-oxopentanoic acid

Synonyms

Pth (1-31) amide; pTH (1-31) amide (human); Parathyroid hormone (1-31) amide; Human parathyroid hormone (1-31) amide; L-Seryl-L-valyl-L-seryl-L-alpha-glutamyl-L-isoleucyl-L-glutaminyl-L-leucyl-L-methionyl-L-histidyl-L-asparaginyl-L-leucylglycyl-L-lysyl-L-histidyl-L-leucyl-L-asparaginyl-L-seryl-L-methionyl-L-alpha-glutamyl-L-arginyl-L-valyl-L-alpha-glutamyl-L-tryptophyl-L-leucyl-L-arginyl-L-lysyl-L-lysyl-L-leucyl-L-glutaminyl-L-alpha-aspartyl-L-valinamide

Sequence

SVSEIQLMHNLGKHLNSMERVEWLRKKLQDV-NH2

InChI

InChI=1S/C162H270N50O46S2/c1-21-86(18)130(211-143(240)101(42-47-124(223)224)190-154(251)117(75-215)207-157(254)127(83(12)13)208-133(230)93(168)73-213)159(256)193-100(41-45-119(170)217)139(236)197-107(60-80(6)7)145(242)191-103(49-56-259-19)141(238)202-112(65-89-71-178-77-184-89)149(246)204-113(66-120(171)218)150(247)195-105(58-78(2)3)134(231)182-72-122(220)185-95(35-24-27-51-163)135(232)201-111(64-88-70-177-76-183-88)148(245)198-108(61-81(8)9)146(243)203-114(67-121(172)219)151(248)206-116(74-214)155(252)194-104(50-57-260-20)160(257)258-126(227)48-43-102(192-156(253)128(84(14)15)209-142(239)98(38-31-55-180-162(175)176)187-132(229)92(167)39-46-123(221)222)140(237)200-110(63-87-69-181-94-34-23-22-32-90(87)94)147(244)199-109(62-82(10)11)153(250)212-158(255)129(85(16)17)210-152(249)115(68-125(225)226)205-138(235)99(40-44-118(169)216)189-144(241)106(59-79(4)5)196-137(234)97(37-26-29-53-165)188-136(233)96(36-25-28-52-164)186-131(228)91(166)33-30-54-179-161(173)174/h22-23,32,34,69-71,76-86,88-89,91-93,95-117,127-130,181,213-215H,21,24-31,33,35-68,72-75,163-168H2,1-20H3,(H2,169,216)(H2,170,217)(H2,171,218)(H2,172,219)(H,182,231)(H,185,220)(H,186,228)(H,187,229)(H,188,233)(H,189,241)(H,190,251)(H,191,242)(H,192,253)(H,193,256)(H,194,252)(H,195,247)(H,196,234)(H,197,236)(H,198,245)(H,199,244)(H,200,237)(H,201,232)(H,202,238)(H,203,243)(H,204,246)(H,205,235)(H,206,248)(H,207,254)(H,208,230)(H,209,239)(H,210,249)(H,211,240)(H,221,222)(H,223,224)(H,225,226)(H4,173,174,179)(H4,175,176,180)(H,212,250,255)/t86-,88?,89?,91-,92-,93-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,127-,128-,129-,130-/m0/s1

InChI Key

OXZNHYPGOAWYLT-FISSOZIDSA-N

Canonical SMILES

CCC(C)C(C(=O)NC(CCC(=O)N)C(=O)NC(CC(C)C)C(=O)NC(CCSC)C(=O)NC(CC1C=NC=N1)C(=O)NC(CC(=O)N)C(=O)NC(CC(C)C)C(=O)NCC(=O)NC(CCCCN)C(=O)NC(CC2C=NC=N2)C(=O)NC(CC(C)C)C(=O)NC(CC(=O)N)C(=O)NC(CO)C(=O)NC(CCSC)C(=O)OC(=O)CCC(C(=O)NC(CC3=CNC4=CC=CC=C43)C(=O)NC(CC(C)C)C(=O)NC(=O)C(C(C)C)NC(=O)C(CC(=O)O)NC(=O)C(CCC(=O)N)NC(=O)C(CC(C)C)NC(=O)C(CCCCN)NC(=O)C(CCCCN)NC(=O)C(CCCNC(=N)N)N)NC(=O)C(C(C)C)NC(=O)C(CCCNC(=N)N)NC(=O)C(CCC(=O)O)N)NC(=O)C(CCC(=O)O)NC(=O)C(CO)NC(=O)C(C(C)C)NC(=O)C(CO)N

1. Investigational parathyroid hormone receptor analogs for the treatment of osteoporosis

Stergios A Polyzos, Polyzois Makras, Zoe Efstathiadou, Athanasios D Anastasilakis Expert Opin Investig Drugs. 2015 Feb;24(2):145-57. doi: 10.1517/13543784.2015.973021. Epub 2014 Oct 15.

Introduction: Intermittent parathyroid hormone (PTH) administration, acting through multiple signaling pathways, exerts an osteoanabolic effect on the skeleton that surpasses the effect of other antiosteoporotic agents. However, its efficacy is limited by the coupling effect and relatively common adverse events. Thus, the development of more sophisticated PTH receptor analogs seems imperative. Areas covered: In this review, the authors summarize the role of PTH signaling pathway in bone remodeling. The authors also summarize investigational analogs targeting this pathway, which may be potential treatments for osteoporosis. Expert opinion: β-arrestins are multifunctional cytoplasmic molecules that are decisive for regulating intracellular PTH signaling. Recently, in preclinical studies, arrestin analogs have achieved the anabolic bone effect of PTH without an accompanying increase in bone resorption. However, it is not yet known whether these analogs have adverse effects and there are no clinical data for their efficacy to date. On the other hand, several molecules derived either from PTH and PTH-related protein (PTHrP) molecules have been developed. Alternative routes of PTH 1 - 34 delivery (oral, transdermal), the PTH analog ostabolin and the N-terminal PTHrP analogs PTHrP 1 - 36 and abaloparatide, have recently been or are currently being tested in clinical trials and are more likely to become available for use in the near future.

2. Stimulation of the growth of femoral trabecular bone in ovariectomized rats by the novel parathyroid hormone fragment, hPTH-(1-31)NH2 (Ostabolin)

J F Whitfield, P Morley, G E Willick, V Ross, J R Barbier, R J Isaacs, L Ohannessian-Barry Calcif Tissue Int. 1996 Feb;58(2):81-7. doi: 10.1007/BF02529728.

The human parathyroid hormone, hPTH-(1-84), and its hPTH-(1-34) fragment are promising anabolic agents for treating osteoporosis because they can strongly stimulate the production of biomechanically effective cortical and trabecular bone in osteopenic ovariectomized (OVX) rats and trabecular bone in osteoporotic postmenopausal humans. The ideal PTH fragment for treating osteoporosis would be the smallest and functionally simplest fragment that activates only one signal mechanism and still strongly stimulates trabecular bone growth. A new PTH fragment, hPTH-(1-31)NH2, which only stimulates adenylyl cyclase instead of stimulating both adenylyl cyclase and phospholipase-C as do hPTH-(1-84) and hPTH-(1-34), is this minimum, high-potency anabolic fragment. hPTH-(1-31)NH2 (which we have named Ostabolin) can greatly thicken trabeculae and increase the dry weight and calcium content of trabecular bone in the distal femurs of osteopenic, young, sexually mature OVX Sprague-Dawley rats when injected subcutaneously each day for 6 weeks at doses between 0.4 and 1.6 nmole/100 g of body weight.

3. Osteoporosis-treating parathyroid hormone peptides: What are they? What do they do? How might they do it?

James F Whitfield Curr Opin Investig Drugs. 2006 Apr;7(4):349-59.

The first experiments demonstrating parathyroid hormone's (PTH's) dramatic bone-building activity in rat pups, using a bovine parathyroid extract called parathormone were reported 74 years ago. Over the next decades, the native parathyroid hormone (human (h)PTH(1-84)) was purified and two of its fragments (hPTH(1-34) and (Leu27)cycloGlu22-Lys26hPTH(1-31)NH2) have been developed for the treatment of osteoporosis. One of these, recombinant (r)hPTH(1-34), is now on the market under the trade name of Forteo. The native hormone has also completed clinical trials and (Leu27)cycloGlu22-Lys26hPTH(1-31)NH2 is in phase II clinical trials under the trade name Ostabolin-C. All three of these peptides potently stimulate bone growth, reinforce bone microstructure weakened by estrogen deprivation and reduce further fracturing. Furthermore, future studies may demonstrate that these peptides also promote the repair of existing fractures and implant anchorage in both healthy and osteoporotic humans. PTHs have the potential to become more successful by using cost-cutting, but still effective, cyclical treatment regimens and by formulating them for non-injectable delivery. This review will discuss the identification of PTH peptides, how they function and their future role in the treatment of osteoporosis.