16.antagonisti estrogena,antiestrogeni,androgeni,anabolici,antiandrogeni,gestageni,oralni...
DESCRIPTION
Farmaceutska hemijaTRANSCRIPT
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ON
C2H5
C2H5
Cl
ON
C2H5
C2H5
TRANS CIS
ANTAGONISTI ESTROGENA
DERIVATI STILBENA
DERIVATI TRIFENILETILENA
Cl
E – ENKLOMIFEN Z – KLOMIFEN
ZUKLOMIFEN
KLOMIFEN – 2-[4- (2-hloro-1,2-difeniletenil)fenoksi]N,N-dietiletanamin
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ON
C2H5
C2H5
Cl
ON
C2H5
C2H5
KLOMIFEN – smeša dva izomera
TRANS CIS
Cl
E – ENKLOMIFEN
ANTIESTROGEN-na uterusAGONIST- na koštano tkivo
Z – ZUKLOMIFEN
ESTROGEN- slab agonist
PARCIJALNI AGONISTA
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TAMOKSIFEN
ON
CH3
CH3
1
Z – 2[4-(1,2-difenilbutenil)fenoksi]-N,N-dimetiletanamin
Z – ANTIESTROGEN – na ES-receptore dojke
E – ESTROGEN – agonist – na ES-receptore uterusa
H3C
2
3
4
1'
2'3'
4'
HO
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TAMOKSIFEN
PARCIJALNI AGONISTA
ON
CH3
CH3
METABOLIT
H3C
1
2
3
4
1'
2'3'
4'
4-OH
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ANTIESTROGEN
• TOREMIFEN
• Parcijalni agonistO
NCH3
CH3CH3Cl
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ON
C O
SERMs – selektivni modulatori estrogenih receptora
RALOKSIFEN
C O
S
OH
HO
DERIVAT BENZOTIOFENA
SELEKTIVNI MODULATOR
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RALOKSIFEN
• SELEKTIVNI MODULATOR
• Antagonist na ES – receptor endometrijuma I dojke
• Osobine agoniste na koštano tkivo i • Osobine agoniste na koštano tkivo i kardiovaskularni sistem
• Prevencija osteoporoze u menopauzi
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Inhibitori aromataza
• Aromataze katalizuju konverziju
• Androstendione u estron i
• Testosterona u estradiol
• Hemijski – podela:• Hemijski – podela:
- steroidni
- nesteroidni
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Steroidni
CH3
CH3
O
H
OH
O
HH
Formestan – kompetitivni inhibitor aromataza
Ireverzibilni, parenteralni
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Nesteroidni
• Derivati triazola
• Letrozol –
• 4,4`-(1H-1,2,4 –
triazol-1-ilmetilen) N
N
N
triazol-1-ilmetilen)
• dibenzonitrilN
NC CN
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CH3
CH3
H
H HAB
C D
5
17
18
19
CH
CH3
OH
H
ANDROGENI HORMONI
ANDROSTAN (C19)
O
CH3 H
H H
ANDROSTAN (C19)
TESTOSTERON
17β-hidroksi-androst-4-en-3-on
3-ON-4-EN17β-ol
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O
CH3
CH3
OH
H
H H
O
CH3
CH3
OH
H
H H
H
5αααα-reduktaze
5αααα-DHT5αααα-DHT
III
STANOLON
BIOLOŠKI AKTIVAN
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Konformacija
CH3
CH3
OH
O
A C DB
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OH
CH3
CH3
O
H H
H
O
CH3
CH3
O
H H
H
[O] 17ββββ-DEHIDROGENAZE
3333αααα,,,, 3333ββββ-ol5555αααα,,,, 5555ββββ
A B
CD
METABOLIZAM
O
CH3
HO
H
H
CH3
HO
H
H
CH3
HO
H
H
4-ANDROSTENDION
3333αααα,,,, 5555αααα 3333αααα,,,, 5555ββββ 3333ββββ,,,, 5555αααα
5αααα-ANDROSTERON(10% AKTIVNOSTI)
(1:2)
5ββββ-ETIOHOLANOLON EPIANDROSTERON
A BA B A B
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Preparati
• Testosteron
• - transdermalni flasteri
• - gelovi
• - implanti ( pelete) • - implanti ( pelete)
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ESTRI TESTOSTERONA
ESTRI-PROPIONAT
- CIPIONAT
- ENANTAT
H3C COOH7 1
RO
CH3
CH3
OH
H
H H
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ESTRI TESTOSTERONA
HO
CH3
CH3
OH
CH3
H
H H
ESTRI-PROPIONAT
- CIPIONAT
- ENANTAT
-BISESTRI
H3C COOH7 1
R
METANDRIOL
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POLUSINTETSKI
OH
CH3
CH3
O
CH3
H H
H
OH
CH3
CH3
O
HO CH3
F H
H
O
CH3
CH3
OH
CH3
H
H H
FLUOKSIMESTRON(1:1 – 2:1)
METANDROSTENOLON(1:1)
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9
17
CH3
CH3
OH
H
H H
9αF POJAČANA AKTIVNOST
17β-ESTAR(PARENTERALNA PRIMENA)
17α-R (ALKIL)(PER-OS PRIMENA
H H
O
5α-REDUKCIJAPOJAČANA AKTIVNOST
USLOV
ZA DEJSTVO
SAR -ANDROGENI
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ANABOLICI
1) DERIVATI 5α-ANDROSTANA
2) DERIVATI 17α-ALKIL-5α-ANDROSTANA2) DERIVATI 17α-ALKIL-5α-ANDROSTANA
3) DERIVATI 17α-METIL-TESTOSTERONA
4) DERIVATI 19-NOR-TESTOSTERONA
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DERIVATI 5α-ANDROSTANA
102
13CH3
CH3
O
H
H H
H
O
H3C
C
O
CH2 CH3
H
101
13CH3
CH3
OH
H
H H
HCH3
OH
MESTEROLON (per os)
DROSTANOLON(3:1 – 4:1)
CH3
CH3
OH
H
H H
HCH3
OH
A
CH3
CH3
OH
H
H H
H
OH
METENOLON
alkil (-CH3)
-1,2-
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DERIVATI 17α-ALKIL-5α-ANDROSTANA - PER-OS
STANOZOLOL(3:1 – 6:1)
LAKTON
OKSANDROLON(2,5 : 1)
a
b
12
3
4
5
67
AB
C DCH3
CH3
OH
H
H H
CH3
HN
N
H
AO
CH3
CH3
OH
H
H H
CH3
OH
OKSIMETOLON
1
3
2
CH3
CH3
OH
H
H H
CH3
PROMENE
2
CH3
CH3
OH
H
H H
CH3
O
CHHO
H
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Nomenklatura
1
C DCH3
CH3
OH
H
CH3
a
b
12
3
4
5
67
AB
H HHN
N
H
17 ββββ–hidroksi 17 α - metil –androstano[3,2-c]-pirazolili17-metil-2`H-androst -2en[3,2,c]-pirazol -17-ol
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17α-ALKIL DERIVATI TESTOSTERONA
1. FLUOKSIMESTRON
2. METANDROSTENOLON
CH3
CH3
OH
H
H H
CH3
H H
O
OH
5
67
CH3
CH3
OH
H
H H
CH3
O CH3
OKSIMESTRON
BOLASTERON
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17
18
19
H
CH3
OH
H
H H
H
O
19 NOR DERIVATI TESTOSTERONA
NANDROLON – 19-NOR TESTOSTERON
(2:1 – 4:1)
DEKANOAT
FENPROPIONAT
17
18
19
H
CH3
OH
H
H H
R
O
FENPROPIONAT
R = CH3 – NORMETANDRON
CH2CH3 - NORETANDRON
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18
19
20 21
H
CH3
OH
H
H H
CH2CH3
OHCH3
ETILESTRENOL
(17α)-19NORPREGNA-4-EN-17-OL
1317
18
19
20 21
H
CH2
OH
H
H H
CH2CH3
O NORBOLETON
13-ETIL-17-HIDROKSI-18,19-DINOR-PREGNA-4-EN-3-ON
(22:1)
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CH3
CH3
OH
H
ESTARPARENTERALNA PRIMENA
ELIMINACIJA CH3 (19)↑ AKTIVNOST
CH2 – IZOSTERNA ZAMENA SA O↑ AKTIVNOST
17α-ALKIL
↓PER-OS AKTIVNOST
H H
O
2,3 → HETEROCIKLUS↑ AKTIVNOST
5α-REDUKTAZA↑ AKTIVNOST
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O
CH3
CH3
H3CO
OCOCH3
12
34
56
7
89
10
1112
13
1415
16
17
18
19
20
21
ANTIANDROGENI – steroidne strukture
3’
Cl
6α-HLOR-17α-HIDROKSI-1α,2α-METILEN-4,6-PREGNADIEN-3,20-DION-17-ACETAT
ILI
6-HLORO-1,2-DIHIDRO-17-HIDROKSI-3’H-CIKLOPROPA[1.2]PREGNA-
1,4,6-TRIEN-3,20-DION
CIPROTERON ACETAT
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N H
C O
C RH3C
CH3
ANILID
1
2
3
N
N
O O
H CH3
CH2R
F C
ANTIANDROGENI - NESTEROIDNI
F3C
NO2
F3C
NO2
R = H FLUTAMID NILUTAMID R = H
R = OH R = OH
HIDANTOIN ANALOG
FLUTAMIDA
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Bikalalutamid
HN S
O OOHH3C
F3C
ONC F
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INHIBITORI 5α-REDUKTAZA
O
5α-reduktaza
OH
5α-DHT
O CH3
INHIBICIJA
N
CH3
CH3
O
H
H
H H
NH C
3
CH3
CH3H
12
43
FINASTERID (PROSCAR )
NHO
4-AZA STEROID
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CH3
CH3
NO
H CF3
CF3
H
2002. Dutasterid
NO
HH
H
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R'O
17
LIPOFILAN
SAR – ZA INHIBITORE 5α-REDUKTAZA
NO
R3-KETO-4-AZA ili
3-EN-3-COOH
7ββββ-METIL (toleriše se)
H ili CH3 ("mala")
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CH3
CH3
C
CH3
H
H H
20 O
GESTAGENI ≡ PROGESTINI
H H
O
PREGNA-4-EN-3,20-DION
PROGESTERON
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CH3
CH3
CH2
CH3
H
H H
OH
8
9
10
1112
13
14 15
1617
18
19
20
21
12
34
56
7A B
CD
C
CH3
1820
21
O
C21-PREGNAN
CH3
CH3
C
H
H H
OH
8
9
10
13
14
18
19
A
O
O
3-on-4-en
4-PREGNEN-3,20-DION
(PROGESTERON)
17α-HIDROKSIPROGESTERON
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CH3
CH3
O
C
OH
O
CH3
H H
H
17
6δδδδ−δδδδ+
AKTIVAN METABOLIT
17α-HIDROKSIPROGESTERON
3α, 3β5α, 5β20α, 20β
PREGNANDIOL
glavni ekskretorni
metabolit
CH3
CH3
HO
C OH
CH3
H H
H
17
H
H
3α, 5β
20α 20(S)
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CH3
CH3
O
C
4
A
O
CH3
H H
H
5
18
19
20
20αααα (20S)20ββββ
C
CH3
OHH
O4
CH3
O3αααα
3ββββ OHH5αααα
5ββββ H
3-ketoreduktaza
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CH3
CH3
O
C
O C
O
(CH2)4
O
CH3
CH3
H H
H
O
CO CH3
KAPROAT = HEKSANOAT
POLUSINTETSKI
CH3
CH3
O
C
O C
4
O
CH3
O
CH3
H H
H
-X (Cl)-R (CH3)
6
POLUSINTETSKI
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CH3
CH3
O
C O
CH3
OH
6
18
19
20
21
17
A
*
C
O
CH3estrar
-CH3 -R-Cl -X
CH3
CH3
O
C O
CH3
O C
O
CH3
CH3
Medroksiprogesteronacetat
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Hlormadinonacetat
CH3
O CH3
O CH3
CH3
Cl
O
OH
H H
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Oralni kontraceptivi
• 1. Derivati 17α-estradiola
• 2. Derivati 17α-hidroksiprogesterona• 2. Derivati 17α-hidroksiprogesterona
• 3.Derivati 19-nortestosterona
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18
17
HO
CH3
OH
R
A
R = -CH3
C CH
3
I DERIVATI ESTRADIOLA
CH3
OH
C CH
ETAR CH3 O
OO
C
H3C
CH
MESTRANOL
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II DERIVATI 17αααα-OH PROGESTERONA
CH3
CH3
O
C
O C
O
CH3
O
CH3
CH3
25x aktivniji
MEDROGSIPROGESTERON ACETAT
CH3
CH3
O
C
O C
4
O
CH3
O
CH3
CH3
67
MEGESTROL ACETAT
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CH3
H
O
OH
C C H
18
19
20 21
19 NOR DERIVATI TESTOSTERONA
20-in
NORETINDRON- 17-α-ETINIL-19-NORTESTOSTERON
CH3
H
OH
C C H
*
OH
CH2 CH CH2
LINESTRENOLALILESTRENOL
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CH2
H
O
OH
C CH
CH3
20 21
13
NORGESTREL
17-HIDROKSI- 18,19-DINOR-13-ETILPREGNA-4-EN-20-IN-3-ON
H
O
O
C CH
C
O
CH3
C
O
H3C
17-HIDROKSI- 18,19-DINOR-13-ETILPREGNA-4-EN-20-IN-3-ON
ETINODIOLDIACETAT
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Drospirenon
CH3 H
O
O
H3C
CH3
O
H
H
H
3-okso-6β,7β:15β,16β-dimetilen-17α-pregna-4-en-21,17- karbolakton
GESTAGEN
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ANTIBEBI PILULA
ESTROGEN (µg)
+
ESTROGEN (µg)
+
PROGESTERON (mg) 19-NORTESTOSTERON (mg)
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H
CH3
OH
H
H H
O
R
R = zasiæen -C2H5
-CH -CH3
ANABOLIK
R = nezasiæen
GESTAGEN(oralni kontraceptiv)
C CH